2-Fluoro-5-nitrophenylboronic acid, pinacol ester → 4-(2-Fluoro-5-nitrophenyl)nicotinonitrile

HRID 2184048Notes

Reaction equation

HRID 2184048 reaction equation
Br[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1.[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1B1OC(C)(C)C(C)(C)O1>>[F:10][C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][C:12]=1[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol esterHCID 223295224-Bromopyridine-3-carbonitrile

Product 1

HCID 223295054-(2-Fluoro-5-nitrophenyl)nicotinonitrile

Procedure

4-Bromonicotinonitrile (1.0 g, 5.5 mmol) was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (1.9 g, 7.1 mmol) using the method in Example 51. Purification by chromatography on silica gel eluting with dichloromethane gave 4-(2-fluoro-5-nitrophenyl)nicotinonitrile as a white solid: δH (400 MHz, CDCl3) 7.44-7.52 (2H, m), 8.38-8.47 (2H, m), 8.95 (1H, d, J 5), 9.06 (1H, s).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane

Sources & evidence

ORD record
ord-20d17789d71d48749c6817666cd55990
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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