872041-85-5

Basic information

• Product Name: Boronic acid,B-(5-chloro-3-pyridinyl)-
• Synonyms: Boronicacid, (5-chloro-3-pyridinyl)- (9CI);(3-Chloro-5-pyridyl)boronic acid;(5-Chloropyridin-3-yl)boronic acid
• CAS NO: 872041-85-5
• Molecular Formula: C₅H₅BClNO₂
• Molecular Weight: 157.3627
• EINECS: 677-212-0
• Product Categories: Heteroaryl Boronic Acids;Boronic Acids;Boronic Acids and Derivatives;Chemical Synthesis;Organometallic Reagents;Organoborons;Pyridine;blocks;BoronicAcids;Pyridines
• Mol File: 872041-85-5.mol
• Article Data: 0

Chemical Properties

• Melting Point: 255-260℃
• Boiling Point: 335.3 °C at 760 mmHg
• Flash Point: 156.6 °C
• Appearance: /
• Density: 1.41 g/cm³
• Refractive Index: 1.559
• Storage Temp.: 2-8°C
• PKA: 5.91±0.10(Predicted)
• CAS DataBase Reference: Boronic acid,B-(5-chloro-3-pyridinyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Boronic acid,B-(5-chloro-3-pyridinyl)-(872041-85-5)
• EPA Substance Registry System: Boronic acid,B-(5-chloro-3-pyridinyl)-(872041-85-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26
• WGK Germany: 3
• Hazardous Substances Data: 872041-85-5(Hazardous Substances Data)

Usage

Uses

5-Chloro-3-pyridineboronic acid can be used as an intermediate:In the preparation of positron emission tomography (PET) radioligand [11C]MK-1064, which is applicable in the orexin-2 receptor imaging.In the synthesis of orexin 2 receptor antagonist (2-SORA) MK-1064.In the preparation of pyridyl-cycloalkyl derived microsomal prostaglandin E synthase-1 inhibitors.In the synthesis of ATAD2 bromodomain inhibitors.

InChI:InChI=1/C5H5BClNO2/c7-5-1-4(6(9)10)2-8-3-5/h1-3,9-10H

Synthetic route

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + methyl 2-chloro-5-iodo-3-pyridinecarboxylate (78686-83-6) → methyl 5′,6-dichloro-[3,3′-bipyridine]-5-carboxylate (1207253-05-1)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In water; N,N-dimethyl-formamide at 25℃; for 18h; Suzuki Coupling;	99%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In water; N,N-dimethyl-formamide at 20℃; Suzuki Coupling;	90%
With caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In water; N,N-dimethyl-formamide at 25℃; for 24h; Suzuki Coupling;

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + 1-ethyl-3-(5-iodo-4-(3-(trifluoromethyl)-1H-pyrazol-1-yl)pyridin-2-yl)urea → C17H14ClF3N6O

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In 1,4-dioxane; water at 80℃; Inert atmosphere;	96%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + 4-methyl-2-oxo-2H-chromen-7-yl-1,1,2,2,3,3,4,4,4-nonafluorobutane-1-sulfonate (93131-78-3) → 7-(5-chloropyridin-3-yl)-4-methyl-2H-chromen-2-one

Conditions	Yield
With 1,3-bis-(diphenylphosphino)propane; palladium diacetate; tetra-n-butylammoniumfluoride trihydrate In methanol; 1,2-dimethoxyethane at 20 - 80℃; for 0.5h; Suzuki-Miyaura Coupling; Inert atmosphere; Microwave irradiation;	90%

2-ethyl-3-O-(tert-butyldimethylsilyl)estrone (767351-13-3) + (5-chloro-3-pyridyl)boronic acid (872041-85-5) → 4-((8S,9S,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-2-ethyl-13-methyl-7,8,9,11,12,13,14,15-octahydro-6H-cyclopenta[a]phenanthren-17-yl)-5-chloro-3-pyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran; water at 60℃; Suzuki-Miyaura Coupling; Inert atmosphere;	90%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + 2-bromoimidazopyrazine → 2-(5-chloropyridin-3-yl)-1H-imidazo[4,5-b]pyrazine

Conditions	Yield
With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); cesium fluoride In 1,2-dimethoxyethane; water at 100℃; for 0.5h; Suzuki Coupling; Inert atmosphere; Microwave irradiation;	88%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + 4-bromo-N-alpha-[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(2H-tetrazol-5-yl)phenyl]-L-phenylalaninamide + trifluoroacetic acid (76-05-1) → N-alpha-[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-4-(5-chloropyrimidin-3-yl)-N-[4-(2H-tetrazol-5-yl)phenyl]-L-phenylalaninamide trifluoroacetate

Conditions

Yield

Stage #1: 4-bromo-N-alpha-[(trans-4-{[(tert-butoxycarbonyl)amino]methyl}cyclohexyl)carbonyl]-N-[4-(2H-tetrazol-5-yl)phenyl]-L-phenylalaninamide With tetrakis(triphenylphosphine) palladium(0) In 1,2-dimethoxyethane at 20℃; for 0.166667h; Stage #2: (5-chloro-3-pyridyl)boronic acid With sodium carbonate In 1,2-dimethoxyethane; ethanol; water for 3h; Reflux; Stage #3: trifluoroacetic acid In water; acetonitrile

88%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + tert-butyl 3-(3-{[(2R)-2-(4-bromophenyl)-2-cyclopentylacetyl]amino}-2-methylphenyl)propanoate → tert-butyl 3-[3-({(2R)-2-[4-(5-chloropyridin-3-yl)phenyl]-2-cyclopentylacetyl}amino)-2-methylphenyl]propanoate

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In tetrahydrofuran; water Suzuki Coupling;	87%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In tetrahydrofuran at 80℃; for 6h; Suzuki Coupling;	52.9%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + 5-bromo-2-methylthioazole-4-carboxylic acid ethyl ester (1047675-70-6) → ethyl 5-(5-chloropyridin-3-yl)-2-methyl-1,3-thiazole-4-carboxylate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 100℃; Inert atmosphere;	87%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + (S)-N-(3-amino-1-cyano-3-oxopropyl)-3-((4-bromophenyl)sulfonyl)-2,2-dimethylpropanamide → (S)-N-(3-amino-1-cyano-3-oxopropyl)-3-((4-(5-chloropyridine-3-yl)phenyl)sulphonyl)-2,2-dimethylpropanamide

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In water; N,N-dimethyl-formamide at 60℃; Suzuki Coupling;	87%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + para-iodoanisole (696-62-8) → 3-chloro-5-(4-methoxyphenyl)pyridine (1595294-68-0)

Conditions	Yield
With potassium carbonate In ethanol; water at 90℃; for 0.25h; Suzuki Coupling; Microwave irradiation;	86%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + 2-Hydroxyphenylacetic acid (614-75-5) → 2-(5-(5-chloropyridin-3-yl)-2-hydroxyphenyl)acetic acid (1338928-51-0)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 90℃;	85.8%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + C17H9BrO → C22H12ClNO

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 90℃; for 5h; Inert atmosphere;	85.65%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + (R)-6-(3-bromo-phenyl)-6-methyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (1397683-39-4) → (R)-6-[3-(5-chloro-pyridin-3-yl)-phenyl]-6-methyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (1397683-41-8)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane at 150℃; for 0.25h; Inert atmosphere; Microwave irradiation;	81%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + (8-bromo[1,2,4]triazolo[1,5-a]pyridine-2-yl)(1-ethyl-4,5,6,7-tetrahydro-1H-indazol-5-yl)amine trifluoroacetic acid salt → [8-(5-chloropyridin-3-yl)-[1,2,4]triazolo[1,5-a]pyridine-2-yl]-(1-ethyl-4,5,6,7-tetrahydro-1H-indazol-5-yl)amine

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; methanol; water at 90℃; for 16h; Suzuki-Miyaura Coupling; Inert atmosphere;	81%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + 1,3,5-trisbromobenzene (626-39-1) → C21H12Cl3N3

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane at 105℃; Inert atmosphere;	78.6%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + tert-butyl 7-bromo-1′,3,3-trimethyl-6′-oxo-3,4,5′,6′-tetrahydro-1′H,2H-spiro[naphthalene-1,4′-pyrimidine]-2′-ylcarbamat (1338094-63-5) → 2′-amino-7-(5-chloropyridin-3-yl)-1′,3,3-trimethyl-3,4-dihydro-1′H,2H-spiro[naphthalene-1,4′-pyrimidin]-6′(5′H)-one (1338093-21-2)

Conditions	Yield
With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; sodium carbonate In 1,4-dioxane; water for 15h; Suzuki Coupling; Sealed tube; Inert atmosphere; Heating;	78%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + 6'-bromo-5"-methyl-3'H-dispiro[cyclobutane-1,2'-indene-1',2"-imidazol]-4"-amine (1383983-37-6) → 6'-(5-chloropyridin-3-yl)-5"-methyl-3'H-dispiro[cyclobutane-1,2'-indene-1',2"-imidazol]-4"-amine (1383983-38-7)

Conditions	Yield
With potassium carbonate; sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid In 2-methyltetrahydrofuran; water at 90℃; for 0.5h; Inert atmosphere; Microwave irradiation; Sealed vial;	77%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + 2-amino-2'-bromo-6'-methoxy-1-methylspiro[imidazole-4,9'-xanthen]-5(1H)-one formate → 2-amino-2'-(5-chloropyridin-3-yl)-6'-methoxy-1-methylspiro[imidazole-4,9'-xanthen]-5(1H)-one (1338927-54-0)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; Inert atmosphere;	73%

diisopropyl hydrogenphosphonate (1809-20-7) + (5-chloro-3-pyridyl)boronic acid (872041-85-5) → diisopropyl (5-chloro-3-pyridinyl)phosphonate

Conditions	Yield
With triphenylphosphine; palladium dichloride; silver(l) oxide at 100℃; for 2h; Inert atmosphere;	71%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + C24H24BBr3 → C39H33BCl3N3

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane at 105℃; Inert atmosphere;	70%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + ethyl 2-bromopyrazolo[1,5-a]pyrimidine-3-carboxylate → ethyl 2-(5-chloropyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Conditions	Yield
With potassium phosphate; chloro(crotyl)(2-dicyclohexylphosphino-2’,4’,6’-triisopropybiphenyl)palladium(II); XPhos In tetrahydrofuran; water at 65℃; for 3h; Suzuki-Miyaura Coupling; Inert atmosphere;	70%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + (4aS,10aS)-2'-((E)-(dimethylamino)methyleneamino)-1'-methyl-5'-oxo-1,1',3,4,4a,5,5',10a-octahydrospiro[benzo[g]isochromene-10,4'-imidazole]-8-yl trifluoromethanesulfonate → (4aS,10aS)-2'-amino-8-(5-chloropyridin-3-yl)-1'-methyl-1,3,4,4a,5,10a-hexahydrospiro[benzo[g]isochromene-10,4'-imidazol]-5'(1'H)-one 2,2,2-trifluoroacetate

Conditions	Yield
With water; sodium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In 1,4-dioxane at 85℃; for 18h; Inert atmosphere; Capped;	69%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + 5-bromo-1H-pyrrolo[2,3-b]pyridine (183208-35-7) + 4-(N,N-dimethylaminocarbonyl)phenylboronic acid (405520-68-5) → 4-(5-(1H-pyrrolo[2,3-b]pyridin-5-yl)pyridin-3-yl)-N,N-dimethylbenzamide

Conditions	Yield
Stage #1: (5-chloro-3-pyridyl)boronic acid; 5-bromo-1H-pyrrolo[2,3-b]pyridine With bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II); potassium carbonate In 1,4-dioxane; water at 95℃; for 1h; Stage #2: 4-(N,N-dimethylaminocarbonyl)phenylboronic acid In 1,4-dioxane; water at 95℃; for 1h;	69%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + (3R,5S,8R,9S,10S,13S,14S)-3-(dimethylamino)-10,13-dimethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate → (3R,5S,8R,9S,10S,13S,14S)-17-(5-chloropyridin-3-yl)-N,N,10,13-tetramethyl-2,3,4,5,6,7,8,9,10,11,12,13,14,15-tetradecahydro-1H-cyclopenta[a]phenanthren-3-amine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran Suzuki-Miyaura Coupling; Inert atmosphere;	69%

2,5-dibromo-3-nitro-pyridine (15862-37-0) + (5-chloro-3-pyridyl)boronic acid (872041-85-5) → 5-bromo-5’-chloro-3-nitro-2,3’-bipyridine

Conditions	Yield
With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 In tetrahydrofuran at 80℃; for 2h; Suzuki Coupling; Inert atmosphere; Sealed tube;	68%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + N-[5-(7-bromo-8-fluoro-4-oxoquinazolin-3 (4H)-yl)-2-(trifluoromethoxy)phenyl]-1-(morpholin-4-yl)cyclopropane-1-carboxamide → N-{5-[7-(5-chloropyridin-3-yl)-8-fluoro-4-oxoquinazolin-3(4H)-yl]-2-(trifluoromethoxy)phenyl}-1-(morpholin-4-yl)cyclopropane-1-carboxamide

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,2-dimethoxyethane; water; N,N-dimethyl-formamide at 80℃; for 2h; Inert atmosphere;	68%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + (8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl trifluoromethanesulfonate → 3-((3S,8R,9S,10R,13S,14S)-3-((tert-butyldimethylsilyl)oxy)-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-5-chloropyridine

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran; water at 20℃; Suzuki-Miyaura Coupling; Inert atmosphere;	67%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + N-[6-chloro-2-(trifluoromethyl)-3-pyridyl]-2-methylpropanamide → C15H13ClF3N3O

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In 1,4-dioxane; water at 120℃; for 0.5h; Inert atmosphere; Microwave irradiation;	66%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + 6-bromo-5'-methylspiro[chroman-4,2'-imidazol]-4'-amine (1383985-05-4) → 6-(5-chloropyridin-3-yl)-5'-methylspiro[chroman-4,2'-imidazol]-4'-amine (1383982-41-9)

Conditions	Yield
With potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In 1,4-dioxane at 130℃; for 1h; Inert atmosphere; Microwave irradiation;	63%

(5-chloro-3-pyridyl)boronic acid (872041-85-5) + (R)-7-bromo-5',5'-difluoro-3,4,5',6'-tetrahydro-2H-spiro[naphthalene-1,4'-[1,3]oxazin]-2'-amine (1415108-46-1) → (R)-7-(5-chloropyridin-3-yl)-5',5'-difluoro-3,4,5',6'-tetrahydro-2H-spiro[naphthalene-1,4'-[1,3]oxazin]-2'-amine (1415107-58-2)

Conditions	Yield
With caesium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran; water at 80℃; for 0.416667h; Inert atmosphere; Sealed tube;	63%
Stage #1: (5-chloro-3-pyridyl)boronic acid; (R)-7-bromo-5',5'-difluoro-3,4,5',6'-tetrahydro-2H-spiro[naphthalene-1,4'-[1,3]oxazin]-2'-amine With caesium carbonate In tetrahydrofuran; water for 0.0833333h; cross-coupling reaction; Inert atmosphere; Stage #2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In tetrahydrofuran; water at 80℃; for 0.416667h;	63%

Downstream Products

• 1362148-02-4 C₁₉H₁₄ClN₅O₃S 
• 1460300-36-0 C₁₂H₁₁ClN₂O₂S 
• 1460300-29-1 C₁₄H₁₃ClN₂O₃S 
• 1595294-68-0 3-chloro-5-(4-methoxyphenyl)pyridine 
• 1597404-00-6 5''-chloro-N-(3,4-dimethoxybenzyl)-2,2':5',3''-terpyridine-3'-carboxamide 
• 1397683-41-8 (R)-6-[3-(5-chloro-pyridin-3-yl)-phenyl]-6-methyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one 
• 1382994-03-7 N-{1-[5-Chloro-3-(5-chloropyridin-3-yl)-2-methoxyphenyl]ethyl}-9H-purin-6-amine 
• 1380106-58-0 3-[2-chloro-4-(5-chloro-pyridin-3-yl)-phenyl]-N-hydroxy-acrylamide hydrochloride 
• 1338928-54-3 2-(2-(4-bromophenoxy)-5-(5-chloropyridin-3-yl)phenyl)acetic acid 
• 1338928-53-2 methyl 2-(2-(4-bromophenoxy)-5-(5-chloropyridin-3-yl)phenyl)acetate 
• 1338928-52-1 methyl 2-(5-(5-chloropyridin-3-yl)-2-hydroxyphenyl)acetate 
• 1338928-51-0 2-(5-(5-chloropyridin-3-yl)-2-hydroxyphenyl)acetic acid 
• 1338094-75-9 3-(4-bromobenzyl)-7-(5-chloropyridin-3-yl)-3-methyl-3,4-dihydronaphthalen-1(2H)-one 
• 1311263-45-2 (2S',4R')-2'-amino-6-(5-chloropyridin-3-yl)-2-(3-methoxybenzyl)-1',2-dimethylspiro[chroman-4 4'-imidazol]-5'(1'H)-one