2-Fluoro-5-nitrophenylboronic acid, pinacol ester → 3-(2-Fluoro-5-nitrophenyl)isonicotinonitrile

HRID 2184049Notes

Reaction equation

HRID 2184049 reaction equation
Br[C:2]1[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[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[CH:9]=[N:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

Participants

3

Reactant 2

HCID 38332972-Fluoro-5-nitrophenylboronic acid, pinacol esterHCID 110740513-Bromo-4-cyanopyridine

Product 1

HCID 224735603-(2-Fluoro-5-nitrophenyl)isonicotinonitrile

Procedure

3-Bromoisonicotinonitrile (2.0 g, 10.9 mmol) was coupled to 2-(2-fluoro-5-nitrophenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (3.8 g, 14.2 mmol) using the method in Example 51. Purification by chromatography on silica gel eluting with dichloromethane containing 10% isohexane gave 3-(2-fluoro-5-nitrophenyl)isonicotinonitrile as a white solid: δH (400 MHz, CDCl3) 7.46 (1H, t, J 9), 7.71 (1H, dd, J 5 and 1), 8.38-8.46 (2H, m), 8.87 (1H, s), 8.91 (1H, d, J 5).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 10% isohexane

Sources & evidence

ORD record
ord-ed669595585c4441abb260f19f2a1214
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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