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917471-30-8

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917471-30-8 Usage

General Description

5-(prop-1-ynyl)pyridin-3-ylboronic acid is a chemical compound with the formula C8H8BNO2. It is a boronic acid derivative with a pyridine ring substituted by a propynyl group at the 5-position. 5-(prop-1-ynyl)pyridin-3-ylboronic acid is commonly used in organic synthesis as a reagent for Suzuki-Miyaura cross-coupling reactions, which are important in the formation of carbon-carbon bonds. Boronic acids like 5-(prop-1-ynyl)pyridin-3-ylboronic acid are also widely utilized in the development of pharmaceuticals, agrochemicals, and materials science due to their ability to form stable complexes with diols and other Lewis bases. Additionally, this compound has potential applications in the field of bioconjugation, where it can be used to functionalize biomolecules for diagnostic and therapeutic purposes.

Check Digit Verification of cas no

The CAS Registry Mumber 917471-30-8 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 9,1,7,4,7 and 1 respectively; the second part has 2 digits, 3 and 0 respectively.
Calculate Digit Verification of CAS Registry Number 917471-30:
(8*9)+(7*1)+(6*7)+(5*4)+(4*7)+(3*1)+(2*3)+(1*0)=178
178 % 10 = 8
So 917471-30-8 is a valid CAS Registry Number.

917471-30-8SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name (5-(Prop-1-yn-1-yl)pyridin-3-yl)boronic acid

1.2 Other means of identification

Product number -
Other names [5-(5-PROP-1-YNYL-3-PYRIDYL)-3-PYRIDYL]BORONIC ACID

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:917471-30-8 SDS

917471-30-8Synthetic route

3-bromo-5-(prop-1-yn-1-yl)pyridine
917772-69-1

3-bromo-5-(prop-1-yn-1-yl)pyridine

5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

Conditions
ConditionsYield
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine With n-butyllithium; Triisopropyl borate In tetrahydrofuran; hexane; toluene at -40 - -20℃; for 1.5h;
Stage #2: With hydrogenchloride; water In tetrahydrofuran; hexane; toluene
95%
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine With n-butyllithium; Triisopropyl borate In 2-methyltetrahydrofuran; toluene at -50℃; for 1.5h;
Stage #2: With hydrogenchloride; water In 2-methyltetrahydrofuran; toluene at 20℃; for 0.333333h;
Stage #3: With sodium hydroxide In 2-methyltetrahydrofuran; water; toluene
87%
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine With n-butyllithium; Triisopropyl borate In 2-methyltetrahydrofuran; toluene at -50℃; for 1.5h;
Stage #2: With hydrogenchloride; water In 2-methyltetrahydrofuran; toluene
87%
3-bromo-5-(prop-1-yn-1-yl)pyridine
917772-69-1

3-bromo-5-(prop-1-yn-1-yl)pyridine

Triisopropyl borate
5419-55-6

Triisopropyl borate

5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

Conditions
ConditionsYield
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine; Triisopropyl borate With n-butyllithium In 2-methyltetrahydrofuran; toluene at -60℃; for 1.5h;
Stage #2: With hydrogenchloride; water In 2-methyltetrahydrofuran; toluene at -50 - 25℃; for 0.333333h;
Stage #3: With sodium hydroxide In 2-methyltetrahydrofuran; water; toluene
87%
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine; Triisopropyl borate With n-butyllithium In tetrahydrofuran; toluene at -78 - -10℃; Inert atmosphere;
Stage #2: With hydrogenchloride In tetrahydrofuran; water; toluene at 20℃; for 1h;
Stage #3: With sodium hydroxide In tetrahydrofuran; water; toluene pH=7 - 8;
62%
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine; Triisopropyl borate With n-butyllithium In tetrahydrofuran; hexane; toluene at -40 - -20℃; for 0.75h;
Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; water; toluene
Stage #3: With sodium hydroxide In tetrahydrofuran; hexane; water; toluene pH=7;
Stage #1: 3-bromo-5-(prop-1-yn-1-yl)pyridine; Triisopropyl borate With n-butyllithium In tetrahydrofuran; hexane; toluene at -40 - -20℃; for 0.75h;
Stage #2: With hydrogenchloride In tetrahydrofuran; hexane; toluene
3,5-dibromopyridine
625-92-3

3,5-dibromopyridine

5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine; tetrabutyl ammonium fluoride / tetrakis(triphenylphosphine) palladium(0); copper(l) iodide / toluene; tetrahydrofuran / 20 °C / Inert atmosphere
2.1: n-butyllithium; Triisopropyl borate / toluene; tetrahydrofuran / 1.42 h / -78 - 20 °C / Inert atmosphere
2.2: 1 h / 20 °C
2.3: pH 7 - 8
View Scheme
Multi-step reaction with 2 steps
1.1: triethylamine; tetrabutyl ammonium fluoride; copper(l) iodide / tetrakis(triphenylphosphine) palladium(0) / toluene; tetrahydrofuran / 20 °C / Inert atmosphere
2.1: n-butyllithium / toluene; tetrahydrofuran / -78 - -10 °C / Inert atmosphere
2.2: 1 h / 20 °C
2.3: pH 7 - 8
View Scheme
Multi-step reaction with 2 steps
1: copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); tetrabutyl ammonium fluoride; triethylamine / toluene / 20 °C
2: n-butyllithium; Triisopropyl borate; ammonium carbonate / tetrahydrofuran; water; toluene / -40 - -10 °C
View Scheme
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(R)-5-(3-amino-1-(3-bromophenyl)-4-fluoro-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
1383847-15-1

(R)-5-(3-amino-1-(3-bromophenyl)-4-fluoro-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one

(R)-5-(3-Amino-4-fluoro-1-(3-(5-(prop-1-ynyl)pyridin-3-yl)phenyl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
1383846-83-0

(R)-5-(3-Amino-4-fluoro-1-(3-(5-(prop-1-ynyl)pyridin-3-yl)phenyl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one

Conditions
ConditionsYield
With potassium carbonate; sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid In 2-methyltetrahydrofuran; water for 2h; Product distribution / selectivity; Reflux; Inert atmosphere;93%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

C22H33BrN4O5SSi

C22H33BrN4O5SSi

C30H39N5O5SSi
917772-70-4

C30H39N5O5SSi

Conditions
ConditionsYield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; tert-butyl alcohol at 60℃; for 1h;90%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(1R,5S,6R)-5-(5-bromo-2-fluorophenyl)-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine

(1R,5S,6R)-5-(5-bromo-2-fluorophenyl)-5-(difluoromethyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine

(1R,5S,6R)-5-(difluoromethyl)-5-(2-fluoro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)phenyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine

(1R,5S,6R)-5-(difluoromethyl)-5-(2-fluoro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)phenyl)-2-oxa-4-azabicyclo[4.1.0]hept-3-en-3-amine

Conditions
ConditionsYield
With potassium phosphate; bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) In 1,4-dioxane; water at 100℃; for 0.5h; Microwave irradiation;74%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

5-(3-Amino-1-(2-bromopyridin-4-yl)-4-fluoro-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
1383847-32-2

5-(3-Amino-1-(2-bromopyridin-4-yl)-4-fluoro-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one

5-(3-Amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
1383846-82-9

5-(3-Amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one

Conditions
ConditionsYield
With potassium carbonate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; palladium diacetate In 1,4-dioxane; water at 100℃; for 0.25h; Product distribution / selectivity; Microwave irradiation;68%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(S)-tert-butyl-(4-(5-bromo-2-chlorothiophen-3-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidene) carbamate
1392015-39-2

(S)-tert-butyl-(4-(5-bromo-2-chlorothiophen-3-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidene) carbamate

(S)-tert-butyl (4-(2-chloro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)thiophen-3-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidene)carbamate
1392142-94-7

(S)-tert-butyl (4-(2-chloro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)thiophen-3-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidene)carbamate

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In dichloromethane; tert-butyl alcohol at 65℃; for 3h;67%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(1r,4r)-6'-bromo-4-methoxy-4,5''-dimethyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine
1383986-03-5

(1r,4r)-6'-bromo-4-methoxy-4,5''-dimethyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine

(1r,4r)-4-methoxy-4,5''-dimethyl-6'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine
1383983-96-7

(1r,4r)-4-methoxy-4,5''-dimethyl-6'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine

Conditions
ConditionsYield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane; water at 130℃; for 0.333333h;58%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(1r,4r)-4
1522464-61-4

(1r,4r)-4"-amino-6'-bromo-5"-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2"-imidazol]-4-ol

(1r,4r)-4
1522464-76-1

(1r,4r)-4"-amino-5"-methyl-6'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3'H-dispiro[cyclohexane-1,2'-indene-1',2"-imidazol]-4-ol

Conditions
ConditionsYield
With sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid; potassium carbonate In 2-methyltetrahydrofuran; water at 120℃; for 0.666667h; Inert atmosphere; Microwave irradiation;55%
potassium phosphate

potassium phosphate

5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(4S,6S)-4-(5-bromo-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine
1620828-88-7

(4S,6S)-4-(5-bromo-2-fluorophenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

(4S,6S)-4-(2-fluoro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)phenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine
1624604-06-3

(4S,6S)-4-(2-fluoro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)phenyl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

Conditions
ConditionsYield
In 1,4-dioxane; water; ethyl acetate55%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(1r,1'R,4R)-6'-bromo-4-methoxy-5''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazole]-4
1384082-50-1

(1r,1'R,4R)-6'-bromo-4-methoxy-5''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazole]-4"-amine

(1r,1’R,4R)-4-methoxy-5”-methyl-6’-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3’H-dispiro[cyclohexane-1,2’-indene-1’2”-imidazol]-4”-amine
1383982-64-6

(1r,1’R,4R)-4-methoxy-5”-methyl-6’-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3’H-dispiro[cyclohexane-1,2’-indene-1’2”-imidazol]-4”-amine

Conditions
ConditionsYield
With potassium carbonate; sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid In 2-methyltetrahydrofuran; water at 80℃; Inert atmosphere;43%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

5'-bromo-4-methoxy-5
1383982-99-7

5'-bromo-4-methoxy-5"-methyldispiro[cyclohexane-1,2'-[1]benzofuran-3',2"-imidazol]-4"-amine

4-methoxy-5
1383983-02-5

4-methoxy-5"-methyl-5'-[5-(prop-1-yn-1-yl)pyridin-3-yl]dispiro[cyclohexane-1,2'-[1]benzofuran-3',2"-imidazol]-4"-amine

Conditions
ConditionsYield
With caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; ethanol; water42%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

C13H14BrN3O
1049639-30-6

C13H14BrN3O

C21H20N4O
960075-74-5

C21H20N4O

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In 1,4-dioxane; water at 65℃; Suzuki coupling;39%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(1r,4r)-6'-bromo-4-methoxy-5''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazole]-4
1384082-93-2

(1r,4r)-6'-bromo-4-methoxy-5''-methyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazole]-4"-amine

(1r,4r)-4-methoxy-5''-methyl-6'-(5-prop-1-yn-1-ylpyridin-3-yl)-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine
1383982-62-4

(1r,4r)-4-methoxy-5''-methyl-6'-(5-prop-1-yn-1-ylpyridin-3-yl)-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine

Conditions
ConditionsYield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 2-methyltetrahydrofuran; water at 100℃; for 1h; Product distribution / selectivity; Microwave irradiation;36%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(R)-5-(3-bromophenyl)-5-(4-methoxy-3,5-dimethylphenyl)-5H-pyrrolo[3,4-b]pyrazin-7-amine
1260248-30-3

(R)-5-(3-bromophenyl)-5-(4-methoxy-3,5-dimethylphenyl)-5H-pyrrolo[3,4-b]pyrazin-7-amine

(S)-5-(4-methoxy-3,5-dimethylphenyl)-5-(3-(5-(prop-1-ynyl)pyridin-3-yl)phenyl)-5H-pyrrolo[3,4-b]pyrazin-7-amine
1260248-24-5

(S)-5-(4-methoxy-3,5-dimethylphenyl)-5-(3-(5-(prop-1-ynyl)pyridin-3-yl)phenyl)-5H-pyrrolo[3,4-b]pyrazin-7-amine

Conditions
ConditionsYield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 90℃; for 4h; Inert atmosphere;34%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

tert-butyl ((4aR,7aR)-7a-(5-bromo-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate
1415208-88-6

tert-butyl ((4aR,7aR)-7a-(5-bromo-2-fluorophenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate

tert-butyl ((4aR,7aR)-7a-(2-fluoro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)phenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate

tert-butyl ((4aR,7aR)-7a-(2-fluoro-5-(5-(prop-1-yn-1-yl)pyridin-3-yl)phenyl)-4a,5,6,7a-tetrahydro-4H-furo[2,3-d][1,3]thiazin-2-yl)carbamate

Conditions
ConditionsYield
With tert.-butyl lithium; bis-triphenylphosphine-palladium(II) chloride In 1,2-dimethoxyethane; ethanol; water at 90℃; for 0.0833333h;33.7%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

tert-butyl ((4S,6S)-4-(5-bromo-3-chlorothiophen-2-yl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate
1616100-79-8

tert-butyl ((4S,6S)-4-(5-bromo-3-chlorothiophen-2-yl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate

tert-butyl ((4S,6S)-4-(3-chloro-5-(5-(prop-1-ynyl)pyridin-3-yl)thiophen-2-yl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate
1616100-80-1

tert-butyl ((4S,6S)-4-(3-chloro-5-(5-(prop-1-ynyl)pyridin-3-yl)thiophen-2-yl)-6-(3,5-dimethylisoxazol-4-yl)-4-methyl-5,6-dihydro-4H-1,3-thiazin-2-yl)carbamate

Conditions
ConditionsYield
With bis-triphenylphosphine-palladium(II) chloride; caesium carbonate In ethanol; water; N,N-dimethyl-formamide at 90℃; for 1h;33.3%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(S)-tert-butyl (5-(5-bromo-3-chlorothiophen-2-yl)-2,5-dimethyl-1,1-dioxido-1,2,4-thiadiazinan-3-ylidene)carbamate
1286776-58-6

(S)-tert-butyl (5-(5-bromo-3-chlorothiophen-2-yl)-2,5-dimethyl-1,1-dioxido-1,2,4-thiadiazinan-3-ylidene)carbamate

C22H25ClN4O4S2

C22H25ClN4O4S2

Conditions
ConditionsYield
Stage #1: 5-(prop-1-ynyl)pyridin-3-ylboronic acid; (S)-tert-butyl (5-(5-bromo-3-chlorothiophen-2-yl)-2,5-dimethyl-1,1-dioxido-1,2,4-thiadiazinan-3-ylidene)carbamate With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate In water; tert-butyl alcohol at 65℃; Suzuki Coupling; Inert atmosphere;
Stage #2: With di-tert-butyl dicarbonate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 24h;
26%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

6‘-bromo-4
1430422-11-9

6‘-bromo-4"-fluoro-4-methoxy-3‘H-dispiro[cyclohexane-1,2’-indene-1‘,2"-pyrrol]-5"-amine

A

(1r,4r)-4’‘-fluoro-4-methoxy-6’-(5-(prop-1-yn-1-yl)pyridin-3-yl)-3‘H-dispiro[cyclohexane-1,2‘-indene-1,2’‘-pyrrol]-5”-amine
1430422-12-0

(1r,4r)-4’‘-fluoro-4-methoxy-6’-(5-(prop-1-yn-1-yl)pyridin-3-yl)-3‘H-dispiro[cyclohexane-1,2‘-indene-1,2’‘-pyrrol]-5”-amine

B

(1s,4s)-4’‘-fluoro-4-methoxy-6’-(5-(prop-1-yn-1-yl)pyridin-3-yl)-3‘H-dispiro[cyclohexane-1,2‘-indene-1,2’‘-pyrrol]-5”-amine
1430475-32-3

(1s,4s)-4’‘-fluoro-4-methoxy-6’-(5-(prop-1-yn-1-yl)pyridin-3-yl)-3‘H-dispiro[cyclohexane-1,2‘-indene-1,2’‘-pyrrol]-5”-amine

Conditions
ConditionsYield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; for 2h; Suzuki Coupling;A 22%
B 11%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(1r,4r)-6'-bromo-4-methoxy-5',5

(1r,4r)-6'-bromo-4-methoxy-5',5"-dimethyl-3'H-dispiro[cyclohexane-1,2'-indene-1',2"-imidazol]-4"-amine

(1r,4r)-4-methoxy-5',5

(1r,4r)-4-methoxy-5',5"-dimethyl-6'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3'H-dispiro[cyclohexane-1,2'-indene-1',2"-imidazol]-4"-amine

Conditions
ConditionsYield
With sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid; potassium carbonate In 2-methyltetrahydrofuran; water at 90℃; for 0.5h; Inert atmosphere; Sealed tube;16%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(R)-5-(3-Amino-1-(3-bromophenyl)-4-fluoro-1H-isoindol-1-yl)-1,3-dimethylpyridin-2(1H)-one
1383847-31-1

(R)-5-(3-Amino-1-(3-bromophenyl)-4-fluoro-1H-isoindol-1-yl)-1,3-dimethylpyridin-2(1H)-one

5-(3-Amino-4-fluoro-1-(3-(5-(prop-1-ynyl)pyridin-3-yl)phenyl)-1H-isoindol-1-yl)-1,3-dimethylpyridin-2(1H)-one
1383847-10-6

5-(3-Amino-4-fluoro-1-(3-(5-(prop-1-ynyl)pyridin-3-yl)phenyl)-1H-isoindol-1-yl)-1,3-dimethylpyridin-2(1H)-one

Conditions
ConditionsYield
With potassium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane; water at 130℃; for 0.25h; Microwave irradiation;14%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

5-(3-Amino-1-(2-bromopyridin-4-yl)-4-fluoro-1H-isoindol-1-yl)-1,3-diethylpyridin-2(1H)-one
1383847-23-1

5-(3-Amino-1-(2-bromopyridin-4-yl)-4-fluoro-1H-isoindol-1-yl)-1,3-diethylpyridin-2(1H)-one

5-(3-Amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1,3-diethylpyridin-2(1H)-one
1383846-96-5

5-(3-Amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1,3-diethylpyridin-2(1H)-one

Conditions
ConditionsYield
With caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,2-dimethoxyethane; ethanol; water at 150℃; for 0.5h; Microwave irradiation;10%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

7'-bromo-4-methoxy-5''-methyl-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

7'-bromo-4-methoxy-5''-methyl-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

A

(1s,4r)-4-methoxy-5''-methyl-7'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazol]-4''-amine
1521284-53-6

(1s,4r)-4-methoxy-5''-methyl-7'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

B

(1r,4s)-4-methoxy-5''-methyl-7'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazol]-4''-amine
1521297-89-1

(1r,4s)-4-methoxy-5''-methyl-7'-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3',4'-dihydrodispiro[cyclohexane-1,2'-naphthalene-1',2''-imidazol]-4''-amine

Conditions
ConditionsYield
With sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid; potassium carbonate In 2-methyltetrahydrofuran; water at 100℃; Inert atmosphere; Sealed tube; Microwave irradiation;A 4%
B 5%
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(S)-tert-butyl (4-(4-bromothiophen-2-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidene)carbamate
917471-29-5

(S)-tert-butyl (4-(4-bromothiophen-2-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidene)carbamate

C23H26N4O3S
960075-52-9

C23H26N4O3S

Conditions
ConditionsYield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tert-butyl alcohol at 65℃; for 0.75h;
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(R)-4-(3-bromothiophen-2-yl)-2-tert-butyloxycarbamimino-1,4-dimethyl-6-oxo-1,3,8-diazaspiro[5.5]decane-8-methyl
917471-27-3

(R)-4-(3-bromothiophen-2-yl)-2-tert-butyloxycarbamimino-1,4-dimethyl-6-oxo-1,3,8-diazaspiro[5.5]decane-8-methyl

C27H33N5O3S

C27H33N5O3S

Conditions
ConditionsYield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; tert-butyl alcohol at 110℃; for 0.25h; Suzuki Coupling; Microwave irradiation;
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

5-(3-Amino-1-(2-bromopyridin-4-yl)-4-fluoro-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
1383847-32-2

5-(3-Amino-1-(2-bromopyridin-4-yl)-4-fluoro-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one

A

(R)-5-(3-amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
1383847-08-2

(R)-5-(3-amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one

B

(S)-5-(3-amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one
1383847-09-3

(S)-5-(3-amino-4-fluoro-1-(5'-(prop-1-ynyl)-2,3'-bipyridin-4-yl)-1H-isoindol-1-yl)-1-ethyl-3-methylpyridin-2(1H)-one

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / 1,4-dioxane; water / 0.25 h / 100 °C / Microwave irradiation
2: Chiralpak AD-H column / isopropyl alcohol; diethylamine; carbon dioxide / Resolution of racemate; Supercritical fluid
View Scheme
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

(1r,1’R,4R)-4-methoxy-5”-methyl-6’-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3’H-dispiro[cyclohexane-1,2’-indene-1’2”-imidazol]-4”-amine
1383982-64-6

(1r,1’R,4R)-4-methoxy-5”-methyl-6’-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3’H-dispiro[cyclohexane-1,2’-indene-1’2”-imidazol]-4”-amine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 2-methyltetrahydrofuran / 1 h / 100 °C / Microwave irradiation
2: ethanol / 18.5 h / 20 - 55 °C
3: sodium hydroxide / dichloromethane; water / 0.25 h / 25 °C
View Scheme
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

A

(1r,1'S,4S)-4-methoxy-5''-methyl-6'-(5-prop-1-yn-1-ylpyridin-3-yl)-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine
1384082-96-5

(1r,1'S,4S)-4-methoxy-5''-methyl-6'-(5-prop-1-yn-1-ylpyridin-3-yl)-3'H-dispiro[cyclohexane-1,2'-indene-1',2''-imidazol]-4''-amine

B

(1r,1’R,4R)-4-methoxy-5”-methyl-6’-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3’H-dispiro[cyclohexane-1,2’-indene-1’2”-imidazol]-4”-amine
1383982-64-6

(1r,1’R,4R)-4-methoxy-5”-methyl-6’-[5-(prop-1-yn-1-yl)pyridin-3-yl]-3’H-dispiro[cyclohexane-1,2’-indene-1’2”-imidazol]-4”-amine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 2-methyltetrahydrofuran / 1 h / 100 °C / Microwave irradiation
2: diethylamine / carbon dioxide; methanol
View Scheme
5-(prop-1-ynyl)pyridin-3-ylboronic acid
917471-30-8

5-(prop-1-ynyl)pyridin-3-ylboronic acid

A

C20H18O8*C26H28N4O

C20H18O8*C26H28N4O

B

C20H18O8*C26H28N4O

C20H18O8*C26H28N4O

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium carbonate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / water; 2-methyltetrahydrofuran / 1 h / 100 °C / Microwave irradiation
2: ethanol / 18.5 h / 20 - 55 °C
View Scheme

917471-30-8Relevant articles and documents

4,6-DIARYLAMINOTHIAZINES AS BACE1 INHIBITORS AND THEIR USE FOR THE REDUCTION OF BETA-AMYLOID PRODUCTION

-

Page/Page column 32; 33, (2014/07/08)

Compounds of formula (I), including pharmaceutically acceptable salts thereof, are set forth herein: (I) wherein R1 and R2 are independently hydrogen, or -CH3; or R1 and R2 can join together in a ring by adding -(CH2)4-; R3 is hydrogen or C1-C3 al-kyl; Y and Z are independently a C6-C10- aryl group or a 5-10 membered heterocyclic group which can be further substituted with from 0-3 substituents selected from the group of halogen, hydroxy, amino, C1-4 alkylamino, C1-4 dialkylamino, halo C1-4 alkyl, CN, C1-C6, alkyl or cycloalkyl, C1-C6 alkoxy, -C=OC1-4 alkyl, -SO2C1-4 alkyl, and C2-C4 alkynyl; A is selected from the group of phenyl, ben-zyl, oxazolyl, thiazolyl, isoxazolyl, imidazolyl, pyrazolyl, pyridyl, pyrimidinyl, and pyrazinyl groups which can be further substituted with from 0-3 substituents selected from the group of halogen, hydroxy, amino, C1-4 alkylamino, C1-4 dialkylamino, haloC1-4 alkyl, hydroxyC1-6 alkyl, CN, C1-C6 alkyl or cycloalkyl, C1-C6 alkoxy, and C2-C4 alkynyl; L is -NHCO-, or is a single bond; and L and Z to-gether can be absent

CYCLOHEXANE-1,2'-NAPHTHALENE-1',2"-IMIDAZOLE COMPOUNDS AND THEIR USE AS BACE INHIBITORS

-

, (2014/01/09)

Cyclohexane-1,2'-naphthalene-1',2''-imidazole compounds, therapeutically acceptable salts thereof, processes for preparation thereof, therapeutic uses of such compounds for treating Aβ-related pathologies such as Down's syndrome, β-amyloid angiopathy, Alzheimer's disease, memory loss, attention deficit symptoms associated with Alzheimer's disease, neurodegeneration associated with diseases such as Alzheimer's disease or dementia including dementia of mixed vascular and degenerative origin, pre-senile dementia, senile dementia and dementia associated with Parkinson's disease, progressive supranuclear palsy or cortical basal degeneration, methods of therapy using such compounds, and pharmaceutical compositions containing such compounds.

COMPOUNDS FOR THE REDUCTION OF BETA-AMYLOID PRODUCTION

-

Page/Page column 34-35, (2012/12/13)

Compounds of formula (I), including pharmaceutically acceptable salts thereof, are set forth herein: wherein R1, R2, R3, R4, R5, and R6 are independently hydrogen, C1-C6 alkyl or C1-C6 cycloalkyl; Y and Z are independently a C6-C10- aryl group or a 5-10 membered heterocyclic group, wherein each Y and Z group can be optionally substituted with from 0-3 substituents selected from halogen, amino, C1-4alkylamino, C1-4dialkylamino, haloC1-4 alkyl, OH, CN, C1-C6 alkyl or cycloalkyl, C1-C6 alkoxy, and C2-C4 alkynyl; L is either a bond or is -NHCO-; L and Z together can be absent; and m is 1, 2 or 3.

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