1692-25-7

Basic information

• Product Name: 3-Pyridylboronic acid
• Synonyms: RARECHEM AH PB 0251;PYRIDIN-3-YLBORONIC ACID;PYRIDIN-3-BORONIC ACID;PYRIDIN-3-YL-3-BORONIC ACID;PYRIDYL-3-BORONIC ACID;PYRIDINE-3-BORONIC ACID;AKOS BRN-0272;3-PYRIDYLBORONIC ACID
• CAS NO: 1692-25-7
• Molecular Formula: C₅H₆BNO₂
• Molecular Weight: 122.92
• EINECS: -0
• Product Categories: blocks;BoronicAcids;Pyridines;Pyridine;Boronic Acids & Esters;Boronic acids;Heterocyclic Compounds;Boronic acid;Organoborons;Aromatics Compounds;B (Classes of Boron Compounds);Boronic acid series;Aromatics;Boron Derivatives;Heterocycles;Boronic Acids & Esters;Boronic Acids;Boronic Acids and Derivatives;Heteroaryl;Boronic Acids and Derivatives;Chemical Synthesis;Heteroaryl Boronic Acids;Organometallic Reagents;OLED materials,pharm chemical,electronic;Boronate Ester;Potassium Trifluoroborate
• Mol File: 1692-25-7.mol
• Article Data: 36

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 308.8 ºC at 760 mmHg
• Flash Point: 140.5 ºC
• Appearance: White to yellow-orange/Powder, Crystals and/or Chunks
• Density: 1.23 g/cm³
• Vapor Pressure: 0.000288mmHg at 25°C
• Refractive Index: 1.534
• Storage Temp.: 0-6°C
• Solubility: Slightly soluble in methanol.
• PKA: 4.00±0.10(Predicted)
• BRN: 471943
• CAS DataBase Reference: 3-Pyridylboronic acid(CAS DataBase Reference)
• NIST Chemistry Reference: 3-Pyridylboronic acid(1692-25-7)
• EPA Substance Registry System: 3-Pyridylboronic acid(1692-25-7)

Safety Data

• Hazard Codes: Xn,Xi,C,F
• Statements: 36/37/38-22-34-11
• Safety Statements: 36/37/39-3-26-45-16
• WGK Germany: 3
• HazardClass: IRRITANT, KEEP COLD
• Hazardous Substances Data: 1692-25-7(Hazardous Substances Data)

Usage

Chemical Properties

Light Yellow Powder

Uses

Different sources of media describe the Uses of 1692-25-7 differently. You can refer to the following data:
1. 3-Pyridylboronic acid is a reagent used for? ;Phosphine-free Suzuki-Miyaura cross-coupling reactions 1 ;Regioselective Suzuki-Miyaura coupling and tandem palladium-catalyzed intramolecular aminocarbonylation and annulation 2 ;N-arylation using copper acetylacetonate catalyst 3 ;Copper-mediated cyanation and regioselective cyanation of electron-rich benzenes 4 Reagent use in Preparation of ? ;New linear poly(phenylpyridyl) chains by Suzuki coupling 5 ;Oligopyridyl foldamers as mimics of a-helix twist 6 ;Many highly significant therapeutic enzymatic and kinase inhibitors and r
2. suzuki reaction

Synthesis Reference(s)

The Journal of Organic Chemistry, 64, p. 3846, 1999 DOI: 10.1021/jo9819279Tetrahedron Letters, 43, p. 4285, 2002

InChI:InChI=1/C5H6BNO2/c8-6(9)5-2-1-3-7-4-5/h1-4,8-9H

Synthetic route

3-Bromopyridine (626-55-1) + n-butyllithium (109-72-8, 29786-93-4) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
Stage #1: 3-Bromopyridine; n-butyllithium In toluene at -50℃; Stage #2: With Triisopropyl borate In tetrahydrofuran at -50 - -15℃;	98%

3-Bromopyridine (626-55-1) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
Stage #1: 3-Bromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 20℃; for 2h; Stage #2: With tris(trimethylsilyl)borate In tetrahydrofuran at 0 - 20℃; for 24h; Stage #3: With hydrogenchloride at 0℃; pH=6 - 7;	75%
Stage #1: 3-Bromopyridine With n-butyllithium In tetrahydrofuran; hexane; toluene at -50℃; Stage #2: With Triisopropyl borate In tetrahydrofuran; hexane; toluene at -50 - -15℃; Stage #3: With sodium hydroxide In tetrahydrofuran; hexane; toluene	73%
With n-butyllithium; Triisopropyl borate In tetrahydrofuran at -78℃; for 3h;	71%

3-Bromopyridine (626-55-1) + Triisopropyl borate (5419-55-6) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
Stage #1: 3-Bromopyridine With n-butyllithium In tetrahydrofuran; hexanes; toluene at -60 - -50℃; for 0.75h; Stage #2: Triisopropyl borate With hydrogenchloride In tetrahydrofuran; hexanes; water; toluene at -50 - -15℃;	73%
With n-butyllithium In tetrahydrofuran; hexane; toluene at -40℃; for 1.5h;
Stage #1: 3-Bromopyridine With n-butyllithium In tetrahydrofuran; hexane; toluene at -60 - -50℃; for 0.583333h; Stage #2: Triisopropyl borate In tetrahydrofuran; hexane; toluene at -15℃;

pyridine (110-86-1) + Trimethyl borate (121-43-7) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
Stage #1: pyridine With lithium diisopropyl amide In diethyl ether at -78℃; for 1h; Stage #2: Trimethyl borate In diethyl ether at 20℃; for 1h;	65%

lithium methanolate (865-34-9) + 4'-bromo-2,2':6',2''-terpyridine (149817-62-9) + 2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-5,5-dimethyl-1,3,2-dioxaborinane (201733-56-4) → 6′,6″-di(pyridin-2-yl)-2,2′:4′,4″:2″,2′′′-quaterpyridine (128143-86-2) + 3-pyridylboronic acid (1692-25-7) + 4′-methoxy-2,2′:6′,2′′-terpyridine (181866-50-2) + 4'-((neopentyl glycolato)boron)-2,2':6',2''-terpyridine (381218-94-6)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride In methanol at 55℃; for 18h;

diisopropyl 3-pyridylboronate → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
With hydrogenchloride In tetrahydrofuran; hexane; toluene at -20 - 20℃;
With hydrogenchloride at 0℃; pH=5 - 6;
With hydrogenchloride In tetrahydrofuran; hexane; water
With water; sodium hydroxide at 30℃; for 3h; Time; Temperature;

3-Bromopyridine (626-55-1) + K4[Fe(CN)6] → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
Multi-step reaction with 2 steps 1: n-BuLi / tetrahydrofuran; hexane; toluene / -40 - -20 °C 2: aq. HCl / tetrahydrofuran; toluene; hexane / -20 - 20 °C View Scheme

3-Bromopyridine (626-55-1) + Trimethyl borate (121-43-7) + ethanol (64-17-5) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
With n-butyllithium; acetic acid In diethyl ether; hexane; water
With n-butyllithium; acetic acid In diethyl ether; hexane; water

3-Bromopyridine (626-55-1) + Trimethyl borate (121-43-7) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid
With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid
With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid
With hydrogenchloride; sodium hydroxide; n-butyllithium In diethyl ether; hexane; water; acetic acid

3-Bromopyridine (626-55-1) + Trimethyl borate (121-43-7) + tert.-butyl lithium (594-19-4) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In methanol; diethyl ether; dichloromethane; pentane
With hydrogenchloride; sodium hydroxide In methanol; diethyl ether; dichloromethane; pentane

3-Bromopyridine (626-55-1) + hydrogenchloride (7647-01-0) + Triisopropyl borate (5419-55-6) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
In tetrahydrofuran (N2); addn. of 1.1 equiv. of butyllithium in hexanes to THF soln. of bromoarene deriv. at -78°C, stirring for 60-120 min at -78°C,addn. of 1.1 equiv. of borate deriv., warming to room temp. overnight; addn. of 2 M aq. HCl, extn (CH2Cl2), recrystn.;

C8H13Cl2N5 + 4-fluoroaniline (371-40-4) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran; water; acetone at 20℃; for 16h;

pyridine-3-boronic acid dimethyl ester (175885-77-5) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
With hydrogenchloride In water at -15℃;

pyridin-3-ylamine (462-08-8) + tetrahydroxydiboron (13675-18-8) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
Stage #1: pyridin-3-ylamine With hydrogenchloride; sodium nitrite In water at 0℃; for 0.25h; Stage #2: tetrahydroxydiboron With potassium carbonate In water at 20℃; for 0.333333h;

3-iodopyridine (1120-90-7) + tetrahydroxydiboron (13675-18-8) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
In methanol; water at -5℃; for 0.166667h; UV-irradiation; Flow reactor; chemoselective reaction;	100 %Spectr.

Trimethyl borate (121-43-7) + pyridin-3-ylmagnesium bromide (21970-14-9) → 3-pyridylboronic acid (1692-25-7)

Conditions	Yield
at 10 - 20℃; for 0.5h;

2,6-dichloropyridine (2402-78-0) + 3-pyridylboronic acid (1692-25-7) → N,N'-bis(3-pyridyl)-2,6-diaminopyridine (70650-96-3)

Conditions	Yield
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0); tricyclohexylphosphine In 1,4-dioxane; water at 100℃; for 18h;	100%

2-Bromo-5-trifluoromethylaniline (454-79-5) + 3-pyridylboronic acid (1692-25-7) → 2-(pyridin-3-yl)-5-(trifluoromethyl)benzeneamine (158461-54-2)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h; Suzuki cross-coupling; Inert atmosphere;	100%
With sodium carbonate; trans-bis(triphenylphosphine)palladium dichloride In 1,4-dioxane; water for 24h; Suzuki cross-coupling; Heating;	91%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In water; acetonitrile at 100℃; for 14h; Inert atmosphere;	7.62 g
With potassium phosphate; methanesulfonic acid(2-dicyclohexylphosphino-2′,4′,6′-triisopropyl-1,1′-biphenyl)[2-(2′-amino-1,1′-biphenyl)]palladium(II) In 1,4-dioxane; water at 80℃; Inert atmosphere;

3-(6-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine (863783-61-3) + 3-pyridylboronic acid (1692-25-7) → 5,6-Dimethyl-3-(6-pyridin-3-yl-quinolin-4-yloxy)-[2,2']bipyridine

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 70℃; for 3h;	100%

3-(7-bromo-quinolin-4-yloxy)-5,6-dimethyl-[2,2']bipyridine (863783-73-7) + 3-pyridylboronic acid (1692-25-7) → 5,6-Dimethyl-3-(7-pyridin-3-yl-quinolin-4-yloxy)-[2,2']bipyridine

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In water; N,N-dimethyl-formamide at 70℃; for 5h;	100%

3-pyridylboronic acid (1692-25-7) + 1-(3-Bromophenyl)ethanone (2142-63-4) → 3-(pyridin-3-yl)acetophenone (171092-38-9)

Conditions	Yield
With sodium tetrachloropalladate(II); 3-(di-tert-butylphosphino)-propane-1-sulfonic acid; sodium carbonate In 2-methyltetrahydrofuran at 80℃; for 4h; Inert atmosphere;	100%
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 20h; Suzuki coupling; Inert atmosphere;	90%

1-Bromo-3-iodobenzene (591-18-4) + 3-pyridylboronic acid (1692-25-7) → 3-(3'-bromophenyl)pyridine (4422-32-6)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In 1,4-dioxane; water at 100℃; Inert atmosphere;	100%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene for 18h; Reflux;	90.9%
With palladium diacetate; sodium carbonate; triphenylphosphine In 1,2-dimethoxyethane; water for 18h; Inert atmosphere; Reflux;	88%

1,3-dibromo-5-chlorobenzene (14862-52-3) + 3-pyridylboronic acid (1692-25-7) → 3,3’-(5-chloro-1,3-phenylene)dipyridine (1214345-76-2)

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

2-bromo-4-methoxyaniline (32338-02-6) + 3-pyridylboronic acid (1692-25-7) → 3-(2-amino-5-methoxyphenyl)pyridine (923293-14-5)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h; Suzuki cross-coupling; Inert atmosphere;	100%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,4-dioxane; water at 80℃; for 2.5h; Suzuki coupling; Inert atmosphere;	100%

3-iodo-1,8-dimethoxyanthracene-9,10-dione (1353384-15-2) + 3-pyridylboronic acid (1692-25-7) → 1,8-dimethoxy-3-(pyridin-3'-yl)-anthraquinone (1353384-35-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In N,N-dimethyl-formamide at 70 - 80℃; Suzuki coupling; Inert atmosphere;	100%

2-(8-Bromo-2-oxo-5,6-dihydro-4H-imidazo[4,5,1-ij]quinolin-1(2H)-yl)-N-methyl-N-phenylacetamide + 3-pyridylboronic acid (1692-25-7) → C24H22N4O2

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 20℃; for 2.5h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;	100%

5-(3-bromophenyl)-3-methoxy-5-(4-methoxyphenyl)pyrrolidin-2-one (1436712-97-8) + 3-pyridylboronic acid (1692-25-7) → 3-methoxy-5-(4-methoxyphenyl)-5-(3-(pyridin-3-yl)phenyl)pyrrolidin-2-one (1436713-00-6)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 90℃; Inert atmosphere;	100%

tert-butyl (5-bromo-2-oxo-1,3-benzoxazol-3(2H)-yl)acetate (863724-27-0) + 3-pyridylboronic acid (1692-25-7) → tert-butyl [2-oxo-5-(pyridin-3-yl)-1,3-benzoxazol-3(2H)-yl]acetate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane at 20℃; for 2h; Suzuki-Miyaura Coupling; Reflux; Inert atmosphere;	100%

methyl 2-chloro-5-iodo-3-pyridinecarboxylate (78686-83-6) + 3-pyridylboronic acid (1692-25-7) → C12H9ClN2O2 (1214383-62-6)

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In water; N,N-dimethyl-formamide at 25℃; Suzuki Coupling;	100%

3-Bromothiophene (872-31-1) + potassium phosphate + bis(di-tert-butyl(3,5-di-(tert-butyl)phenyl)phosphine)dichloropalladium + 3-pyridylboronic acid (1692-25-7) + butan-1-ol (71-36-3) → 3-(thiophen-3-yl)pyridine (21308-81-6)

Conditions	Yield
In water	100%

tert-butyl (2S)-2-[(S)-hydroxy{3-[(trifluoromethanesulfonyl)oxy]phenyl}methyl]piperidine-1-carboxylate (1007110-00-0) + 3-pyridylboronic acid (1692-25-7) → tert-butyl (2S)-2-{(S)-hydroxy[3-(pyridin-3-yl)phenyl]-methyl}piperidine-1-carboxylate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; N,N-dimethyl-formamide for 1.5h; Heating;	100%

2-((trans-4-hydroxycyclohexyl)amino)-4-(4-iodo-3-isopropyl-1H-pyrazolo[3,4-b]pyridin-1-yl)benzonitrile + 3-pyridylboronic acid (1692-25-7) → 2-((trans-4-hydroxycyclohexyl)amino)-4-(3-isopropyl-4-(pyridin-3-yl)-1H-pyrazolo[3,4-b]pyridin-1-yl)benzonitrile (1260536-06-8)

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane; water at 100℃; for 4h; Suzuki-Miyaura Coupling; Inert atmosphere;	100%

tert-butyl 3-(3-(3-bromophenyl)-1H-pyrazol-5-yl)pyrrolidine-1-carboxylate + 3-pyridylboronic acid (1692-25-7) → tert-butyl 3-(3-(3-(pyridin-3-yl)phenyl)-1H-pyrazol-5-yl)pyrrolidine-1-carboxylate

Conditions	Yield
With tetrakis(triphenylphosphine) palladium(0); caesium carbonate In tetrahydrofuran; water at 100℃; for 16h;	100%

4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (941685-08-1) + 3-pyridylboronic acid (1692-25-7) → 4-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

Conditions	Yield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water Inert atmosphere;	99.9%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 60℃; for 5h; Inert atmosphere;	99.9%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 60℃; for 5h; Inert atmosphere;	99.9%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In 1,4-dioxane; water at 60℃; for 5h; Inert atmosphere;	99.9%

2-bromothiophene (1003-09-4) + 3-pyridylboronic acid (1692-25-7) → 3-thiophen-2-yl-pyridine (21298-53-3)

Conditions	Yield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 20h; Suzuki coupling; Inert atmosphere;	99%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,2-dimethoxyethane at 90℃; for 1h; Suzuki coupling;	62%
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 80℃; for 24h; Suzuki-Miyaura coupling; Reflux;	62%
With bis(η3-allyl-μ-chloropalladium(II)); N,N,N′,N′-tetra(diphenylphosphinomethyl)-1,2-ethylenediamine; potassium carbonate In N,N-dimethyl acetamide; butan-1-ol at 120℃; for 12h; Reagent/catalyst; Time; Suzuki Coupling; Inert atmosphere;

bromobenzene (108-86-1) + 3-pyridylboronic acid (1692-25-7) → 3-phenylpyridine (1008-88-4)

Conditions	Yield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 6h; Suzuki coupling; Inert atmosphere;	99%
With C18H20Cl2N8Pd; caesium carbonate In 1,4-dioxane at 100℃; for 12h; Suzuki coupling; Inert atmosphere;	96%
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0); tricyclohexylphosphine In 1,4-dioxane; water at 100℃; for 18h;	95%

4-n-butylchlorobenzene (15499-27-1) + 3-pyridylboronic acid (1692-25-7) → 3-(4-n-butylphenyl)pyridine (732276-73-2)

Conditions	Yield
With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; tris(dibenzylideneacetone)dipalladium (0) In butan-1-ol at 100℃; for 15h; Suzuki-Miyaura coupling;	99%
With potassium phosphate; tris(dibenzylideneacetone)dipalladium (0); tricyclohexylphosphine In 1,4-dioxane; water at 100℃; for 18h;	93%

2-methylphenyl bromide (95-46-5) + 3-pyridylboronic acid (1692-25-7) → 3-(p-methylphenyl)pyridine (90395-49-6)

Conditions	Yield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 3h; Suzuki coupling; Inert atmosphere;	99%
With C18H20Cl2N8Pd; caesium carbonate In 1,4-dioxane at 100℃; for 12h; Suzuki coupling; Inert atmosphere;	91%
With potassium carbonate; (1RS,2RS,3SR,4SR)-1,2,3,4-tetrakis((diphenylphosphanyl)methyl)cyclopentane; bis(η3-allyl-μ-chloropalladium(II)) In xylene at 130℃; for 20h; Suzuki coupling reaction;	85%
With potassium carbonate; [Pd(C3H5)Cl]2/Tedicyp complex In xylene at 130℃; for 20h; Suzuki reaction;	85%

4-bromo-2-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-1-methoxybenzene (927384-45-0) + 3-pyridylboronic acid (1692-25-7) → 3-(2,3-dihydro-1H-naphtho[1,8-de]-1,3,2-diazaborinyl)-4-methoxy-1-(3-pyridyl)benzene

Conditions	Yield
With cesium fluoride; bis(tri-t-butylphosphine)palladium(0) In 1,4-dioxane; water at 80℃; for 4h; Suzuki-Miyaura reaction;	99%
With cesium fluoride; bis(tri-t-butylphosphine)palladium(0) In not given at 60°C;	99%

3-pyridylboronic acid (1692-25-7) + 3-benzyloxy-4-iodo-5-(1-methoxycarbonyl-4-piperidyl)isoxazol (841259-40-3) → 3-benzyloxy-4-(3-pyridyl)-5-(1-methoxycarbonyl-4-piperidinyl)isoxazole

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; potassium carbonate In N,N-dimethyl-formamide at 70℃; for 22h; Suzuki coupling;	99%

3-pyridylboronic acid (1692-25-7) + 4-bromo-aniline (106-40-1) → 4-pyridin-3-ylaniline (82261-42-5)

Conditions	Yield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 20h; Suzuki coupling; Inert atmosphere;	99%
With potassium phosphate tribasic heptahydrate In 1,4-dioxane for 48h; Suzuki coupling; Reflux;	85%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water for 3.5h; Inert atmosphere;	71%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 100℃; Inert atmosphere;	40%
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate In 1,4-dioxane; water at 100℃; Suzuki Coupling; Inert atmosphere;	35%

3-bromo-2,6-dimethoxypyridine (13445-16-4) + 3-pyridylboronic acid (1692-25-7) → 2,6-dimethoxy-3-(3-pyridinyl)pyridine (1169827-10-4)

Conditions	Yield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 20h; Suzuki coupling; Inert atmosphere;	99%

3-methoxyphenyl bromide (2398-37-0) + 3-pyridylboronic acid (1692-25-7) → 3-(3-methoxyphenyl)pyridine (4373-67-5)

Conditions	Yield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 6h; Suzuki coupling; Inert atmosphere;	99%

para-bromoacetophenone (99-90-1) + 3-pyridylboronic acid (1692-25-7) → 1-(4-(pyridin-3-yl)phenyl)ethan-1-one (90395-45-2)

Conditions	Yield
With potassium phosphate; palladium dichloride; S-2,2',6,6'-tetramethoxy-4,4'-bis(diphenylphosphino)-3,3'-bipyridine In butan-1-ol at 100℃; for 20h; Suzuki coupling; Inert atmosphere;	99%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 16h; Inert atmosphere;	91.6%
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; water; toluene at 80℃; for 16h; Inert atmosphere;	91.6%

quinolin-8-yl methanesulfonate (916314-51-7) + 3-pyridylboronic acid (1692-25-7) → 8-(3-pyridyl)-quinoline (37049-48-2)

Conditions	Yield
With sodium tetrachloropalladate(II); dicyclohexyl {2-sulfo-9-[3-(4-sulfophenyl)propyl]-9H-fluoren-9-yl}phosphonium hydrogen sulfate; potassium carbonate In water at 95℃; for 16h; Suzuki-Miyaura coupling; Inert atmosphere;	99%

phenyl methanesulfonate (16156-59-5) + 3-pyridylboronic acid (1692-25-7) → 3-phenylpyridine (1008-88-4)

Conditions	Yield
With sodium tetrachloropalladate(II); dicyclohexyl {2-sulfo-9-[3-(4-sulfophenyl)propyl]-9H-fluoren-9-yl}phosphonium hydrogen sulfate; potassium carbonate In water at 95℃; for 16h; Suzuki-Miyaura coupling; Inert atmosphere;	99%

Upstream product

• 626-55-1 3-Bromopyridine 
• 109-72-8 n-butyllithium 
• 121-43-7 Trimethyl borate 
• 7647-01-0 hydrogenchloride 
• 5419-55-6 Triisopropyl borate 
• 21970-14-9 pyridin-3-ylmagnesium bromide 
• 110-86-1 pyridine 
• 1120-90-7 3-iodopyridine 
• 13675-18-8 tetrahydroxydiboron 
• 462-08-8 pyridin-3-ylamine 
• 175885-77-5 pyridine-3-boronic acid dimethyl ester 
• 371-40-4 4-fluoroaniline 
• 594-19-4 tert.-butyl lithium 
• 64-17-5 ethanol 

Downstream Products

• 25660-38-2 1-(pyridin-3-yl)-1H-benzo[d]imidazole 
• 78210-78-3 5-Methyl-2,3'-bipyridyl 
• 26844-80-4 5-methyl-2,3'-bipyridyl 
• 73082-69-6 5-(pyridin-3-yl)pyrimidine 
• 38840-05-0 4-methyl-2,3′-bipyridine 
• 38588-49-7 5-(pyridin-3-yl)-furan-2-carbaldehyde 
• 133531-43-8 5-pyridin-3-yl-thiophene-2-carbaldehyde 
• 837376-40-6 3-(5-nitrothiophen-2-yl)pyridine 
• 6294-65-1 2-pyridin-3-yl-quinoline 
• 840538-72-9 1-benzenesulfonyl-4-methoxy-3-(4-pyridin-3-yl-benzyl)-1H-indole 
• 147621-19-0 6-(pyridin-3-yl)-1H-indole 
• 15862-23-4 [3,3']bipyridinyl-5-ol 
• 1008-88-4 3-phenylpyridine 
• 157402-43-2 3-(2,6-dimethyl-phenyl)-pyridine 

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