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

Description

DIETHYL(3-PYRIDYL)BORANE is an organoborane compound that features a boron atom bonded to two ethyl groups and a 3-pyridyl group. It is known for its unique chemical properties and reactivity, making it a versatile building block in organic synthesis and medicinal chemistry.

Uses

Used in Pharmaceutical Industry:
DIETHYL(3-PYRIDYL)BORANE is used as a reactant for the preparation of inhibitors of ataxia telangiectasia mutated and Rad3 related (ATR) protein kinase. These inhibitors have potential as anticancer agents, targeting key enzymes involved in DNA damage response and cell cycle regulation.
Used in Organic Synthesis:
DIETHYL(3-PYRIDYL)BORANE is used as a reactant in N-Methylation reactions of the pyridyl group, which is crucial for the synthesis of various pharmaceuticals and agrochemicals.
Used in Catalysis:
DIETHYL(3-PYRIDYL)BORANE is used as a reactant in palladium-catalyzed amination reactions, which are important for the formation of carbon-nitrogen bonds in the synthesis of complex organic molecules.
Used in Heck Reactions:
DIETHYL(3-PYRIDYL)BORANE is used as a reactant in intramolecular Heck reactions, a type of carbon-carbon coupling reaction that is useful for the synthesis of cyclic compounds.
Used in Coupling Reactions:
DIETHYL(3-PYRIDYL)BORANE is used as a reactant in coupling reactions, which are essential for the formation of carbon-carbon and carbon-heteroatom bonds in organic synthesis.
Used in Suzuki Reaction:
DIETHYL(3-PYRIDYL)BORANE is used as a reactant in the synthesis of trisubstituted pyrimidines from polyhalopyrimidines via Suzuki coupling, a cross-coupling reaction that allows for the formation of biaryl and heteroaryl compounds with potential applications in materials science and medicinal chemistry.

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 
• 109-72-8 n-butyllithium 
• 1120-87-2 4-bromopyridin 
• 97-94-9 triethyl borane 

Downstream Products

• 581-50-0 2,3'-bipyridine 
• 581-46-4 3,3'-bipyridine 
• 38840-05-0 4-methyl-2,3′-bipyridine 
• 15862-22-3 5-bromo-3,3'-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 
• 19100-10-8 (Z)-2-(but-2-en-2-yl)benzo[d]thiazole 
• 5957-97-1 4-(3'-pyridinyl)-1-chlorobenzene 
• 1008-88-4 3-phenylpyridine 
• 5958-02-1 3-(4-methoxyphenyl)pyridine 
• 94356-83-9 3-(1-Piperidin-1-ylmethyl-vinyl)-pyridine 
• 15825-89-5 3-(1-methylethenyl)pyridine 
• 1121-55-7 3-vinylpyridine 

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