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14490-05-2

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14490-05-2 Usage

Uses

Different sources of media describe the Uses of 14490-05-2 differently. You can refer to the following data:
1. Reactant for preparation of β-carbolines via diastereo- and enantioselective Bronsted acid catalyzed N-acyliminium cyclization cascades 1 Reactant for preparation of substituted tetrahydro-β-carbolines as potential agents for treatment of human papillomavirus infection (HPV) 2 Reactant for asymmetric synthesis of nitrogen heterocycles via Bronsted acid-catalyzed N-acyliminium cyclization cascade 3 Reactant for amidation reactions 4 Reactant for preparation of potent β3-adrenergic receptor agonists 5 Reactant for preparation of tryptamine-based sulfonamides as potent and selective inhibitors of 15-lipoxygenase 6
2. Reactant for preparation of β-carbolines via diastereo- and enantioselective Bronsted acid catalyzed N-acyliminium cyclization cascadesReactant for preparation of substituted tetrahydro-β-carbolines as potential agents for treatment of human papillomavirus infection (HPV)Reactant for asymmetric synthesis of nitrogen heterocycles via Bronsted acid-catalyzed N-acyliminium cyclization cascadeReactant for amidation reactionsReactant for preparation of potent β3-adrenergic receptor agonistsReactant for preparation of tryptamine-based sulfonamides as potent and selective inhibitors of 15-lipoxygenase

Check Digit Verification of cas no

The CAS Registry Mumber 14490-05-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,4,4,9 and 0 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 14490-05:
(7*1)+(6*4)+(5*4)+(4*9)+(3*0)+(2*0)+(1*5)=92
92 % 10 = 2
So 14490-05-2 is a valid CAS Registry Number.
InChI:InChI=1/C11H14N2/c1-8-3-2-4-10-9(5-6-12)7-13-11(8)10/h2-4,7,13H,5-6,12H2,1H3

14490-05-2 Well-known Company Product Price

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  • Aldrich

  • (M8002)  7-Methyltryptamine  

  • 14490-05-2

  • M8002-500MG

  • 1,484.73CNY

  • Detail
  • Aldrich

  • (M8002)  7-Methyltryptamine  

  • 14490-05-2

  • M8002-1G

  • 2,387.97CNY

  • Detail

14490-05-2SDS

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 2-(7-methyl-1H-indol-3-yl)ethanamine

1.2 Other means of identification

Product number -
Other names 2-(7-Methyl-indol-3-yl)-aethylamin

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:14490-05-2 SDS

14490-05-2Synthetic route

(E)-7-methyl-3-(2-nitrovinyl)-1H-indole

(E)-7-methyl-3-(2-nitrovinyl)-1H-indole

7-methyltryptamine
14490-05-2

7-methyltryptamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; Inert atmosphere;99%
With lithium aluminium tetrahydride In tetrahydrofuran
2-(7-methyl-1H-indol-3-yl)acetonitrile
858232-97-0

2-(7-methyl-1H-indol-3-yl)acetonitrile

7-methyltryptamine
14490-05-2

7-methyltryptamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride
3-(2-amino-ethyl)-7-methyl-indole-2-carboxylic acid
14517-83-0

3-(2-amino-ethyl)-7-methyl-indole-2-carboxylic acid

7-methyltryptamine
14490-05-2

7-methyltryptamine

Conditions
ConditionsYield
With hydrogenchloride
4-aminobutyrylaldehyde diethylacetal
6346-09-4

4-aminobutyrylaldehyde diethylacetal

2-methylphenylhydrazine
529-27-1

2-methylphenylhydrazine

7-methyltryptamine
14490-05-2

7-methyltryptamine

Conditions
ConditionsYield
With zinc(II) chloride
7-methyl-1H-indole
933-67-5

7-methyl-1H-indole

7-methyltryptamine
14490-05-2

7-methyltryptamine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: POCl3
2: AcOH
3: LiAH4 / tetrahydrofuran
View Scheme
Multi-step reaction with 3 steps
1.1: trichlorophosphate / 1.5 h / Cooling with ice
1.2: 20 °C / Cooling with ice
1.3: 1 h / 105 °C
2.1: ammonium acetate / Reflux
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: diethyl ether / 18 h / 40 °C
2: ammonia / 1,4-dioxane / 20 °C
3: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / Reflux
View Scheme
Multi-step reaction with 3 steps
1.1: trichlorophosphate / 0.25 h / 0 °C / Inert atmosphere
1.2: 3.25 h / 0 - 20 °C / Inert atmosphere
1.3: 0.08 h / Reflux
2.1: ammonium acetate / 1.5 h / Reflux; Inert atmosphere
3.1: lithium aluminium tetrahydride / tetrahydrofuran / 36 h / 0 - 20 °C / Inert atmosphere
View Scheme
7-methyl-1H-indole-3-carbaldehyde
4771-50-0

7-methyl-1H-indole-3-carbaldehyde

7-methyltryptamine
14490-05-2

7-methyltryptamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: AcOH
2: LiAH4 / tetrahydrofuran
View Scheme
Multi-step reaction with 2 steps
1: ammonium acetate / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: ammonium acetate / 2 h / Reflux
2: lithium aluminium tetrahydride / tetrahydrofuran / 36 h / 0 - 20 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1: ammonium acetate / 1.5 h / Reflux; Inert atmosphere
2: lithium aluminium tetrahydride / tetrahydrofuran / 36 h / 0 - 20 °C / Inert atmosphere
View Scheme
8-methyl-2,3,4,9-tetrahydro-β-carbolin-1-one
14490-04-1

8-methyl-2,3,4,9-tetrahydro-β-carbolin-1-one

7-methyltryptamine
14490-05-2

7-methyltryptamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: aq.-ethanolic KOH
2: aqueous HCl
View Scheme
1-methyl-2-nitrobenzene
88-72-2

1-methyl-2-nitrobenzene

7-methyltryptamine
14490-05-2

7-methyltryptamine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: tetrahydrofuran / 1 h / -40 °C / Inert atmosphere
2.1: trichlorophosphate / 1.5 h / Cooling with ice
2.2: 20 °C / Cooling with ice
2.3: 1 h / 105 °C
3.1: ammonium acetate / Reflux
4.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere
View Scheme
2-(7-methyl-1H-indol-3-yl)-2-oxoacetyl chloride
59022-69-4

2-(7-methyl-1H-indol-3-yl)-2-oxoacetyl chloride

7-methyltryptamine
14490-05-2

7-methyltryptamine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: ammonia / 1,4-dioxane / 20 °C
2: lithium aluminium tetrahydride / tetrahydrofuran / 18 h / Reflux
View Scheme
C11H10N2O2

C11H10N2O2

7-methyltryptamine
14490-05-2

7-methyltryptamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran for 18h; Reflux;
C11H10N2O2
566200-37-1

C11H10N2O2

7-methyltryptamine
14490-05-2

7-methyltryptamine

Conditions
ConditionsYield
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 36h; Inert atmosphere;
With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 36h; Inert atmosphere;
7-methyltryptamine
14490-05-2

7-methyltryptamine

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester
101385-93-7

3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester

8-methyl-2,3,4,9-tetrahydrospiro[β-carboline-1,3'-pyrrolidine] dihydrochloride

8-methyl-2,3,4,9-tetrahydrospiro[β-carboline-1,3'-pyrrolidine] dihydrochloride

Conditions
ConditionsYield
Stage #1: 7-methyltryptamine; 3-oxo-pyrrolidine-1-carboxylic acid tert-butyl ester With acetic acid at 100℃; for 4.5h;
Stage #2: With hydrogenchloride In 1,2-dioxacyclohexane at 20℃;
100%
7-methyltryptamine
14490-05-2

7-methyltryptamine

7-(trifluoromethyl)-3,4,5,6-tetrahydro-2H-azepine
1146222-77-6

7-(trifluoromethyl)-3,4,5,6-tetrahydro-2H-azepine

5-(8-methyl-1-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)pentan-1-amine

5-(8-methyl-1-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)pentan-1-amine

Conditions
ConditionsYield
With trifluoroacetic acid In dichloromethane at 20℃; for 168h; Pictet-Spengler Synthesis;100%
7-methyltryptamine
14490-05-2

7-methyltryptamine

acetic anhydride
108-24-7

acetic anhydride

N-(2-(7-methyl-1H-indol-3-yl)ethyl)acetamide
769186-81-4

N-(2-(7-methyl-1H-indol-3-yl)ethyl)acetamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃; for 1h;99%
7-methyltryptamine
14490-05-2

7-methyltryptamine

2-chloro-ethanol
107-07-3

2-chloro-ethanol

C13H18N2O
1135827-90-5

C13H18N2O

Conditions
ConditionsYield
In dimethyl sulfoxide at 80℃; for 5h;99%
7-methyltryptamine
14490-05-2

7-methyltryptamine

hept-3-ynoic acid
59862-93-0

hept-3-ynoic acid

(11bR)-10-methyl-11b-n-propyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
1178541-69-9

(11bR)-10-methyl-11b-n-propyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Conditions
ConditionsYield
Stage #1: hept-3-ynoic acid With triphenylphosphine gold (I) chloride; silver trifluoromethanesulfonate In toluene at 20℃; for 1h;
Stage #2: 7-methyltryptamine With (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 80 - 110℃; for 48h; optical yield given as %ee; enantioselective reaction;
96%
7-methyltryptamine
14490-05-2

7-methyltryptamine

5-phenylfuran-2(3H)-one

5-phenylfuran-2(3H)-one

(11bS)-10-methyl-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
1178541-62-2

(11bS)-10-methyl-11b-phenyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Conditions
ConditionsYield
With (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 110℃; for 41h; optical yield given as %ee; enantioselective reaction;95%
7-methyltryptamine
14490-05-2

7-methyltryptamine

3-methyllevulinic acid
6628-79-1

3-methyllevulinic acid

(1R,11bR)-1,10,11b-trimethyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
1253404-42-0

(1R,11bR)-1,10,11b-trimethyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Conditions
ConditionsYield
With (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene for 48h; Reflux; optical yield given as %ee; enantioselective reaction;95%
7-methyltryptamine
14490-05-2

7-methyltryptamine

benzaldehyde
100-52-7

benzaldehyde

8-methyl-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline
865681-23-8

8-methyl-1-phenyl-2,3,4,9-tetrahydro-1H-β-carboline

Conditions
ConditionsYield
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In ethyl acetate at 110℃; for 0.166667h; Microwave irradiation; Sealed tube;95%
but-3-yne-1-sulfonyl chloride

but-3-yne-1-sulfonyl chloride

7-methyltryptamine
14490-05-2

7-methyltryptamine

N-[2-(7-methyl-1H-indol-3-yl)ethyl]but-3-yne-1-sulfonamide
1452838-33-3

N-[2-(7-methyl-1H-indol-3-yl)ethyl]but-3-yne-1-sulfonamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at -78℃; Inert atmosphere;95%
7-methyltryptamine
14490-05-2

7-methyltryptamine

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

tert-butyl (2-(7-methyl-1H-indol-3-yl)ethyl)carbamate

tert-butyl (2-(7-methyl-1H-indol-3-yl)ethyl)carbamate

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran at 20℃;95%
7-methyltryptamine
14490-05-2

7-methyltryptamine

(+/-)-3-acetylheptanoic acid
1253404-36-2

(+/-)-3-acetylheptanoic acid

(1R,11bR)-1-butyl-10,11b-dimethyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
1253404-40-8

(1R,11bR)-1-butyl-10,11b-dimethyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Conditions
ConditionsYield
With (R)-3,3'-bis-(triphenylsilyl)octahydrobinolphosphoric acid In toluene for 72h; Reflux; optical yield given as %ee; enantioselective reaction;94%
7-methyltryptamine
14490-05-2

7-methyltryptamine

cinnamyl methyl carbonate
85217-69-2, 87802-71-9

cinnamyl methyl carbonate

N-(2-(7-methyl-1H-indol-3-yl)ethyl)-1-phenylprop-2-en-1-amine
1400791-77-6

N-(2-(7-methyl-1H-indol-3-yl)ethyl)-1-phenylprop-2-en-1-amine

Conditions
ConditionsYield
With C48H49IrNO2P(1+)*CF3O3S(1-) In tetrahydrofuran at 50℃; Schlenk technique; Inert atmosphere;94%
5-methyl-2-furanone
591-12-8

5-methyl-2-furanone

7-methyltryptamine
14490-05-2

7-methyltryptamine

(11bR)-10,11b-dimethyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
1178541-60-0

(11bR)-10,11b-dimethyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Conditions
ConditionsYield
With (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 110℃; for 24h; optical yield given as %ee; enantioselective reaction;92%
7-methyltryptamine
14490-05-2

7-methyltryptamine

2-oxocycloheptaneacetic acid
33366-28-8

2-oxocycloheptaneacetic acid

(5aR,15bR)-14-methyl-2,3,4,5,5a,6,10,15-octahydro-9H-cyclohepta[1,8a]indolizino[8,7-b]indol-7(1H)-one
1253404-47-5

(5aR,15bR)-14-methyl-2,3,4,5,5a,6,10,15-octahydro-9H-cyclohepta[1,8a]indolizino[8,7-b]indol-7(1H)-one

Conditions
ConditionsYield
With (R)-3,3'-bis-(triphenylsilyl)octahydrobinolphosphoric acid In toluene for 48h; Reflux; optical yield given as %ee; enantioselective reaction;91%
7-methyltryptamine
14490-05-2

7-methyltryptamine

ethyl 2-(2-oxocyclohexyl)acetate
24731-17-7

ethyl 2-(2-oxocyclohexyl)acetate

(4aR,14bR)-13-methyl-1,2,3,4,4a,5,9,14-octahydro-6H,8H-pyrido[3,4-b:1,2-i']diindol-6-one
1253404-44-2

(4aR,14bR)-13-methyl-1,2,3,4,4a,5,9,14-octahydro-6H,8H-pyrido[3,4-b:1,2-i']diindol-6-one

Conditions
ConditionsYield
With (R)-3,3'-bis-(triphenylsilyl)octahydrobinolphosphoric acid In toluene for 48h; Reflux; optical yield given as %ee; enantioselective reaction;89%
7-methyltryptamine
14490-05-2

7-methyltryptamine

p-bromophenylpropene methyl carbonate
952686-36-1

p-bromophenylpropene methyl carbonate

1-(4-bromophenyl)-N-(2-(7-methyl-1H-indol-3-yl)ethyl)prop-2-en-1-amine
1400791-80-1

1-(4-bromophenyl)-N-(2-(7-methyl-1H-indol-3-yl)ethyl)prop-2-en-1-amine

Conditions
ConditionsYield
With C48H49IrNO2P(1+)*CF3O3S(1-) In tetrahydrofuran at 50℃; Schlenk technique; Inert atmosphere;87%
7-methyltryptamine
14490-05-2

7-methyltryptamine

N-(2-(7-methyl-1H-indol-3-yl)ethyl)-1-(3-(trifluoromethyl)phenyl)prop-2-en-1-amine
1400791-81-2

N-(2-(7-methyl-1H-indol-3-yl)ethyl)-1-(3-(trifluoromethyl)phenyl)prop-2-en-1-amine

Conditions
ConditionsYield
With C48H49IrNO2P(1+)*CF3O3S(1-) In tetrahydrofuran at 50℃; Schlenk technique; Inert atmosphere;86%
7-methyltryptamine
14490-05-2

7-methyltryptamine

N-ethoxycarbonylphthalimide
22509-74-6

N-ethoxycarbonylphthalimide

2-[2-(7-Methyl-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione
192182-62-0

2-[2-(7-Methyl-1H-indol-3-yl)-ethyl]-isoindole-1,3-dione

Conditions
ConditionsYield
In tetrahydrofuran for 48h; Heating;85%
7-methyltryptamine
14490-05-2

7-methyltryptamine

dec-3-ynoic acid
27007-78-9

dec-3-ynoic acid

(11bR)-11b-hexyl-10-methyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
1178541-61-1

(11bR)-11b-hexyl-10-methyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Conditions
ConditionsYield
Stage #1: dec-3-ynoic acid With triphenylphosphine gold (I) chloride; silver trifluoromethanesulfonate In toluene at 20℃; for 1h;
Stage #2: 7-methyltryptamine With (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 80 - 110℃; for 48h; optical yield given as %ee; enantioselective reaction;
84%
7-methyltryptamine
14490-05-2

7-methyltryptamine

acetophenone
98-86-2

acetophenone

(8-methyl-9H-pyrido[3,4-b]indol-1-yl)(phenyl)methanone

(8-methyl-9H-pyrido[3,4-b]indol-1-yl)(phenyl)methanone

Conditions
ConditionsYield
With dihydrogen peroxide; iodine In water; dimethyl sulfoxide at 110℃;84%
1-oxaspiro(2.5)octane
185-70-6

1-oxaspiro(2.5)octane

7-methyltryptamine
14490-05-2

7-methyltryptamine

C18H26N2O
1135827-71-2

C18H26N2O

Conditions
ConditionsYield
In ethanol at 60℃; for 18h;82%
7-methyltryptamine
14490-05-2

7-methyltryptamine

methyl chloroformate
79-22-1

methyl chloroformate

methyl (2-(7-methyl-1H-indol-3-yl)ethyl)carbamate

methyl (2-(7-methyl-1H-indol-3-yl)ethyl)carbamate

Conditions
ConditionsYield
With sodium hydroxide In ethyl acetate at 20℃;82%
With triethylamine In dichloromethane at 0 - 20℃; for 3h; Inert atmosphere;
With sodium hydroxide In water; ethyl acetate at 20℃; for 1h; Inert atmosphere;
With sodium carbonate In dichloromethane; water for 2h; Inert atmosphere;
7-methyltryptamine
14490-05-2

7-methyltryptamine

hexadec-3-ynoic acid
89199-90-6

hexadec-3-ynoic acid

(11bR)-11b-dodecyl-10-methyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
1178541-70-2

(11bR)-11b-dodecyl-10-methyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Conditions
ConditionsYield
Stage #1: hexadec-3-ynoic acid With triphenylphosphine gold (I) chloride; silver trifluoromethanesulfonate In toluene at 20℃; for 1h;
Stage #2: 7-methyltryptamine With (R)-3,3'-bis(triphenylsilyl)-1,1'-binaphthyl-2,2'-diyl hydrogenphosphate In toluene at 80 - 110℃; for 48h; optical yield given as %ee; enantioselective reaction;
81%
7-methyltryptamine
14490-05-2

7-methyltryptamine

(+/-)-3-ethyl-4-oxopentanoic acid
4439-86-5

(+/-)-3-ethyl-4-oxopentanoic acid

(1R,11bR)-1-ethyl-10,11b-dimethyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
1253404-43-1

(1R,11bR)-1-ethyl-10,11b-dimethyl-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one

Conditions
ConditionsYield
With (R)-3,3'-bis-(triphenylsilyl)octahydrobinolphosphoric acid In toluene for 54h; Reflux; optical yield given as %ee; enantioselective reaction;81%
7-methyltryptamine
14490-05-2

7-methyltryptamine

1-(4-isobutylphenyl)-N-(2-(7-methyl-1H-indol-3-yl)ethyl)prop-2-en-1-amine
1400791-79-8

1-(4-isobutylphenyl)-N-(2-(7-methyl-1H-indol-3-yl)ethyl)prop-2-en-1-amine

Conditions
ConditionsYield
With C48H49IrNO2P(1+)*CF3O3S(1-) In tetrahydrofuran at 50℃; Schlenk technique; Inert atmosphere;78%
methyl crotyl carbonate

methyl crotyl carbonate

7-methyltryptamine
14490-05-2

7-methyltryptamine

N-(2-(7-methyl-1H-indol-3-yl)ethyl)but-3-en-2-amine
1400791-82-3

N-(2-(7-methyl-1H-indol-3-yl)ethyl)but-3-en-2-amine

Conditions
ConditionsYield
With C48H49IrNO2P(1+)*CF3O3S(1-) In tetrahydrofuran at 50℃; Schlenk technique; Inert atmosphere;78%
7-methyltryptamine
14490-05-2

7-methyltryptamine

hept-1-en-3-yl methyl carbonate
1239597-30-8

hept-1-en-3-yl methyl carbonate

N-(2-(7-methyl-1H-indol-3-yl)ethyl)hept-1-en-3-amine
1400791-83-4

N-(2-(7-methyl-1H-indol-3-yl)ethyl)hept-1-en-3-amine

Conditions
ConditionsYield
With C48H49IrNO2P(1+)*CF3O3S(1-) In tetrahydrofuran at 50℃; Schlenk technique; Inert atmosphere;78%
7-methyltryptamine
14490-05-2

7-methyltryptamine

6-(trifluoromethyl)-2,3,4,5-tetrahydropyridine
1146222-76-5

6-(trifluoromethyl)-2,3,4,5-tetrahydropyridine

4-(8-methyl-1-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)butan-1-amine

4-(8-methyl-1-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-1-yl)butan-1-amine

Conditions
ConditionsYield
With camphor-10-sulfonic acid In water at 130℃; for 14h; Pictet-Spengler Synthesis;77%
7-methyltryptamine
14490-05-2

7-methyltryptamine

3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole
85446-05-5

3,6-dibromo-9-(oxiran-2-ylmethyl)-9H-carbazole

1-(3,6-dibromo-9H-carbazol-9-yl)-3-((2-(7-methyl-1H-indol-3-yl)ethyl)amino)propan-2-ol

1-(3,6-dibromo-9H-carbazol-9-yl)-3-((2-(7-methyl-1H-indol-3-yl)ethyl)amino)propan-2-ol

Conditions
ConditionsYield
In ethanol for 12h; Inert atmosphere; Reflux;77%

14490-05-2Relevant articles and documents

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Grandberg,Bobrova

, (1973)

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Asymmetric dearomatization of indoles through a Michael/Friedel-Crafts-Type cascade to construct polycyclic spiroindolines

Zhao, Xiaohu,Liu, Xiaohua,Mei, Hongjiang,Guo, Jing,Lin, Lili,Feng, Xiaoming

supporting information, p. 4032 - 4035 (2015/03/30)

A highly efficient asymmetric dearomatization of indoles was realized through a cascade reaction between 2-isocyanoethylindole and alkylidene malonates catalyzed by a chiral N,N-dioxide/MgII catalyst. Fused polycyclic indolines containing three stereocenters were afforded in good yields with excellent diastereo- and enantioselectivities through a Michael/Friedel-Crafts/Mannich cascade. When 2-substituted 2-isocyanoethylindoles were used, spiroindoline derivatives were obtained through a Michael/Friedel-Crafts reaction.

Exploiting a novel size exclusion phenomenon for enantioselective acid/base cascade catalysis

Muratore, Michael E.,Shi, Lei,Pilling, Adam W.,Storer, R. Ian,Dixon, Darren J.

, p. 6351 - 6353 (2012/07/17)

A novel size exclusion phenomenon between PS-BEMP and sterically bulky BPAs, has been discovered and exploited in a one-pot base-catalysed Michael addition/acid-catalysed enantioselective N-acyliminium cyclisation cascade, allowing the preparation of structurally complex β-carbolines with moderate to good enantiocontrol.

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