89878-14-8

Basic information

• Product Name: DIETHYL(3-PYRIDYL)BORANE
• Synonyms: Diethyl(3-pyridyl)borane,95%;3-(diethylboryl)pyridine, Abiraterone intermediate;DIETHYL(3-PYRIDYL)BORANE;3-(DIETHYLBORYL)PYRIDINE;3-Diethylboranyl Pyridine;3-(diethyboryl)pyridine;Dithyl (3-Pyridyl)borane;Diethyl(3-pyridyl)borane,3-(Diethylboryl)pyridine
• CAS NO: 89878-14-8
• Molecular Formula: C₉H₁₄BN
• Molecular Weight: 147.03
• Product Categories: Nitrogen cyclic compounds;B (Classes of Boron Compounds);Boranes;Organic boronic acid
• Mol File: 89878-14-8.mol
• Article Data: 5

Chemical Properties

• Melting Point: 172-175 °C(lit.)
• Boiling Point: 205.9 °C at 760 mmHg
• Flash Point: 78.3 °C
• Appearance: /Solid
• Density: 0.86 g/cm³
• Vapor Pressure: 0.35mmHg at 25°C
• Refractive Index: 1.457
• Storage Temp.: Refrigerator
• PKA: 4.40±0.12(Predicted)
• Water Solubility: Slightly soluble in water.
• CAS DataBase Reference: DIETHYL(3-PYRIDYL)BORANE(CAS DataBase Reference)
• NIST Chemistry Reference: DIETHYL(3-PYRIDYL)BORANE(89878-14-8)
• EPA Substance Registry System: DIETHYL(3-PYRIDYL)BORANE(89878-14-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39
• WGK Germany: 3
• Hazardous Substances Data: 89878-14-8(Hazardous Substances Data)

Usage

Chemical Properties

White to yellow solid

Uses

Different sources of media describe the Uses of 89878-14-8 differently. You can refer to the following data:
1. Reactant for: preparation of inhibitors of ataxia telangiectasia mutated and Rad3 related (ATR) protein kinase as potential anticancer agents, N-Methylation reactions of the pyridyl group, Palladium catalyzed amination reactions, intramolecular Heck reactions, Coupling reactions and Synthesis of trisubstituted pyrimidines from polyhalopyrimidines via Suzuki coupling.
2. Reactant for:Preparation of inhibitors of ataxia telangiectasia mutated and Rad3 related (ATR) protein kinase as potential anticancer agentsN-Methylation reactions of the pyridyl groupPalladium catalyzed amination reactionsIntramolecular Heck reactionsCoupling reactionsSynthesis of trisubstituted pyrimidines from polyhalopyrimidines via Suzuki coupling
3. suzuki reaction

InChI:InChI=1/C9H14BN/c1-3-10(4-2)9-6-5-7-11-8-9/h5-8H,3-4H2,1-2H3

Synthetic route

3-Bromopyridine (626-55-1) + diethyl methoxy borane (7397-46-8) → 3-Diethylboranylpyridine (89878-14-8)

Conditions	Yield
Stage #1: 3-Bromopyridine With isopropylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Stage #2: diethyl methoxy borane In tetrahydrofuran at 0℃; for 1h;	78%
Stage #1: 3-Bromopyridine With n-butyllithium In hexane; tert-butyl methyl ether at -28℃; Inert atmosphere; Large scale; Stage #2: diethyl methoxy borane In tert-butyl methyl ether at -40 - -32℃; for 8.5h; Inert atmosphere; Large scale;	75%

3-Bromopyridine (626-55-1) + n-butyllithium (109-72-8, 29786-93-4) + diethylmethoxyborane → 3-Diethylboranylpyridine (89878-14-8)

Conditions	Yield
In tetrahydrofuran

4-bromopyridin (1120-87-2) → 3-Diethylboranylpyridine (89878-14-8) + diethyl (pyridin-4-yl)borane (93830-58-1)

Conditions	Yield
With n-butyllithium

3-Bromopyridine (626-55-1) + triethyl borane (97-94-9) → 3-Diethylboranylpyridine (89878-14-8)

Conditions	Yield
With n-butyllithium In diethyl ether; hexane at -78 - 20℃; Inert atmosphere;

3-Bromopyridine (626-55-1) + diethyl methoxy borane (7397-46-8) → 3-Diethylboranylpyridine (89878-14-8)

Conditions	Yield
With n-butyllithium In dibutyl ether

benzyl 7-bromo-3,4-dihydro-1H-isoquinoline-2-carboxylate (625127-09-5) + 3-Diethylboranylpyridine (89878-14-8) → C22H20N2O2 (625127-14-2)

Conditions	Yield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In methanol; water; toluene at 80℃;	100%

3-methoxyphenyl bromide (2398-37-0) + 3-Diethylboranylpyridine (89878-14-8) → 3-(3-methoxyphenyl)pyridine (4373-67-5)

Conditions	Yield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran; water for 4h; Heating / reflux;	99%

3-Diethylboranylpyridine (89878-14-8) + 4-iodo-2-methoxy-1-methylbenzene (220728-62-1) → 3-(3-methoxy-4-methylphenyl)pyridine (702683-21-4)

Conditions	Yield
With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; ethanol; water for 24h; Heating / reflux;	99%

C22H29F3O5S (1382471-65-9) + 3-Diethylboranylpyridine (89878-14-8) → (5S,8R,9S,10S,13S)-10,13-dimethyl-17-(pyridin-3-yl)-2,3,4,5,6,7,8,9,10,11,12,13-dodecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate (1382471-66-0)

Conditions	Yield
With potassium carbonate; bis-triphenylphosphine-palladium(II) chloride In 1,4-dioxane; water at 80℃; Suzuki Coupling; Ultrasonic degassing; Inert atmosphere;	98.5%

5-chloro-2-methyl-benzoic acid ethyl ester (56427-54-4) + 3-Diethylboranylpyridine (89878-14-8) → ethyl 5-(3-pyridyl)-2-methylbenzoate (702682-38-0)

Conditions	Yield
With sodium carbonate; DavePhos; palladium diacetate In tetrahydrofuran; water for 6h; Heating / reflux;	97%

3β-acetoxyandrosta-5,16-dien-17-yl trifluoromethanesulphonate (115375-60-5) + 3-Diethylboranylpyridine (89878-14-8) → abiraterone acetate (154229-18-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran at 65℃; for 4h; Reflux;	95%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 1h; Reflux;	95%
With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In tetrahydrofuran; water at 60℃; for 1h;	94%

3-Diethylboranylpyridine (89878-14-8) + 3,3-dimethyl-6-(3'-methylbut-3'-enyl)-6-methoxycarbonylcyclohexenyl triflate (157520-44-0) → (1R,3aR)-1,6,6-Trimethyl-1-pyridin-3-ylmethyl-1,2,3,4,5,6-hexahydro-indene-3a-carboxylic acid methyl ester

Conditions	Yield
With palladium diacetate; tetraethylammonium chloride; sodium carbonate; triphenylphosphine In toluene Heating;	92%
With tetraethylammonium chloride; sodium carbonate; triphenylphosphine; palladium diacetate In water; toluene for 8h; Cyclization; hetarylation; Heating;	92%

6-chloro-3-pyridinecarboxamide (6271-78-9) + 3-Diethylboranylpyridine (89878-14-8) → 5-carbamoyl-2,3'-bipyridine (164074-61-7)

Conditions	Yield
With potassium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 6h; Heating;	92%

3-Diethylboranylpyridine (89878-14-8) + 6-trifluoromethanesulfonyloxy-3,4-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (171288-01-0) → 5,6-dihydro-4H-[2,3']bipyridinyl-1-carboxylic acid tert-butyl ester

Conditions	Yield
With sodium carbonate; bis-triphenylphosphine-palladium(II) chloride In tetrahydrofuran at 80℃; for 2h; Substitution;	91%

3β-acetoxy-5α-androsta-16-ene-17-yl trifluoromethanesulfonate (91934-55-3) + 3-Diethylboranylpyridine (89878-14-8) → 3β-acetyloxy-17-(3-pyridinyl)-5α-androst-16-ene (219843-76-2)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran at 80℃; for 1h;	90%
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 18h; Suzuki Coupling; Inert atmosphere; Reflux;	90%

3α-acetoxy-5β-androsta-16-ene-17-yl trifluoromethanesulfonate + 3-Diethylboranylpyridine (89878-14-8) → 3α-acetoxy-17-(3-pyridyl)-5β-androsta-16-ene

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water for 18h; Suzuki Coupling; Inert atmosphere; Reflux;	90%

3-Diethylboranylpyridine (89878-14-8) + (2R,3R,4S,5R)-3,4,5-Tris-benzyloxy-2-benzyloxymethyl-6-[1-iodo-meth-(Z)-ylidene]-tetrahydro-pyran (607715-89-9) → (Z)-2,6-anhydro-3,4,5,7-tetra-O-benzyl-1-deoxy-1-(3-pyridyl)-D-gluco-hept-1-enitol

Conditions	Yield
With sodium hydroxide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; water for 3h; B-alkyl Suzuki cross-coupling reaction; Heating;	89%

Phenyl triflate (17763-67-6) + 3-Diethylboranylpyridine (89878-14-8) → 3-phenylpyridine (1008-88-4)

Conditions	Yield
With potassium hydroxide In tetrahydrofuran; water at 60℃; for 0.0833333h; Suzuki-Miyaura Coupling;	89%

C20H27F3O4S + 3-Diethylboranylpyridine (89878-14-8)

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; water at 20 - 75℃; for 0.5h;	88.8%

+ 3-Diethylboranylpyridine → 3-(pyridin-3-yl)phenol (93851-31-1)

Conditions	Yield
Stage #1: 3-Bromophenol; 3-Diethylboranylpyridine With sodium carbonate; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran; ethanol; water at 20℃; for 2 - 20h; Heating / reflux; Stage #2: With hydrogenchloride In tetrahydrofuran; ethanol; water for 0.25h;	88%

1-bromo-4-phenylethynylbenzene (13667-12-4) + 3-Diethylboranylpyridine (89878-14-8) → C19H13N (1064194-22-4)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In N,N-dimethyl-formamide at 80℃; for 3h; Suzuki coupling; Inert atmosphere; Microwave irradiation;	88%

3-Diethylboranylpyridine (89878-14-8) + para-nitrophenyl bromide (586-78-7) → 3-(4'-nitrophenyl)pyridine (4282-46-6)

Conditions	Yield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 2h; Heating;	87%

abiraterone + 3-Diethylboranylpyridine (89878-14-8) → C27H39NOSi

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; ethanol; water; toluene at 20 - 75℃; for 0.5h;	86.2%

bromochlorobenzene (106-39-8) + 3-Diethylboranylpyridine (89878-14-8) → 4-(3'-pyridinyl)-1-chlorobenzene (5957-97-1)

Conditions	Yield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 2h; Heating;	86%

2-bromobenzoic acid methyl ester (610-94-6) + 3-Diethylboranylpyridine (89878-14-8) → 3-(o-carbomethoxyphenyl)pyridine (90395-46-3)

Conditions	Yield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 18h; Heating;	86%
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 3h; Heating;	59%

C25H35F3O5S + 3-Diethylboranylpyridine (89878-14-8) → C29H39NO2

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; ethanol; water; toluene at 20 - 75℃; for 2h;	85.5%

2-bromo-pyridine (109-04-6) + 3-Diethylboranylpyridine (89878-14-8) → 2,3'-bipyridine (581-50-0)

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran for 8h; Heating;	85%

bromobenzene (108-86-1) + 3-Diethylboranylpyridine (89878-14-8) → 3-phenylpyridine (1008-88-4)

Conditions	Yield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 1h; Heating;	85%

1-(2'-Bromo-biphenyl-4-ylmethyl)-1H-[1,2,4]triazole (735333-61-6) + 3-Diethylboranylpyridine (89878-14-8) → 3-(4'-[1,2,4]Triazol-1-ylmethyl-biphenyl-2-yl)-pyridine (735333-63-8)

Conditions	Yield
With sodium carbonate; bis(triphenylphosphine)palladium(II)-chloride In tetrahydrofuran; water at 20 - 80℃; for 24h;	85%

3-Diethylboranylpyridine (89878-14-8) + N'-tosyl phenylhydrazine (29110-75-6) → 3-phenylpyridine (1008-88-4)

Conditions	Yield
With palladium diacetate; potassium carbonate In dimethyl sulfoxide at 60℃; Suzuki Coupling; Inert atmosphere;	85%

C39H41F3O4S + 3-Diethylboranylpyridine (89878-14-8) → C43H45NO

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate In tetrahydrofuran; ethanol; water; toluene at 20 - 75℃; for 0.5h;	85%

3β-acetoxy-5,6-seco-5-keto-17-O-triflyl-androstan-6-al + 3-Diethylboranylpyridine (89878-14-8) → 3β-acetoxy-5-keto-5,6-seco-17-(3-pyridyl)-androst-16-en-6-al

Conditions	Yield
With bis-triphenylphosphine-palladium(II) chloride; sodium hydrogencarbonate In tetrahydrofuran; water at 50℃; for 1h;	85%

1-(2-(4-bromophenyl)ethynyl)-4-methylbenzene (62856-42-2) + 3-Diethylboranylpyridine (89878-14-8) → 3-(4-p-tolylethynyl-phenyl)-pyridine

Conditions	Yield
With potassium hydroxide; tetrabutylammomium bromide; triphenylphosphine; bis(dibenzylideneacetone)-palladium(0) In tetrahydrofuran at 80℃; for 18h;	84.5%

para-bromotoluene (106-38-7) + 3-Diethylboranylpyridine (89878-14-8) → 4-(3-pyridyl)toluene

Conditions	Yield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide In tetrahydrofuran for 2h; Heating;	84%

+ 3-Diethylboranylpyridine

Conditions	Yield
With potassium hydroxide; tetrakis(triphenylphosphine) palladium(0); tetra-(n-butyl)ammonium iodide In tetrahydrofuran for 12h; Heating;	84%
With tetrakis(triphenylphosphine) palladium(0); tetrabutylammomium bromide; sodium hydroxide In tetrahydrofuran; water at 4 - 66℃; Suzuki Coupling; Inert atmosphere; Large scale;

Upstream product

• 626-55-1 3-Bromopyridine 
• 7397-46-8 diethyl methoxy borane 
• 1120-87-2 4-bromopyridin 
• 97-94-9 triethyl borane 
• 109-72-8 n-butyllithium 

Downstream Products

• 581-50-0 2,3'-bipyridine 
• 70650-96-3 N,N'-bis(3-pyridyl)-2,6-diaminopyridine 
• 106047-28-3 6-bromo-2-(3-pyridyl)pyridine 
• 774-53-8 5-bromo-2,3′-bipyridine 
• 5958-02-1 3-(4-methoxyphenyl)pyridine 
• 15825-89-5 3-(1-methylethenyl)pyridine 
• 1121-55-7 3-vinylpyridine 
• 94356-76-0 3-[1-(trimethylsilyl)vinyl]pyridine 
• 90395-45-2 1-(4-(pyridin-3-yl)phenyl)ethan-1-one 
• 13238-38-5 3-(2-phenylethynyl)pyridine 
• 5958-01-0 3-(2-methoxyphenyl)pyridine 
• 154229-18-2 abiraterone acetate 
• 154229-20-6 17-(3-pyridyl)androsta-3,5,16-triene 
• 154229-38-6 3-<2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenoxy>-17-(3-pyridyl)androsta-3,5,16-triene 

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