3'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile → 3'-(7-Difluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile

HRID 478237Notes

Reaction equation

HRID 478237 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([CH:11]([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:22]2[CH:23]=[C:24]([C:28]3[C:29]([C:34]#[N:35])=[CH:30][CH:31]=[CH:32][CH:33]=3)[CH:25]=[CH:26][CH:27]=2)O1>>[F:12][CH:11]([F:13])[C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:26]3[CH:25]=[C:24]([C:28]4[C:29]([C:34]#[N:35])=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:23]=[CH:22][CH:27]=3)=[CH:3][N:4]=[C:5]2[N:10]=1

Participants

3

Reactant 2

HCID 112436553'-(4,4,5,5-Tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrileHCID 180012863-Bromo-7-difluoromethylimidazo[1,2-a]pyrimidine

Product 1

HCID 99461753'-(7-Difluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrileYield 58%

Procedure

3-Bromo-7-difluoromethylimidazo[1,2-a]pyrimidine (248 mg, 1.00 mmol) was coupled with 3′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 1 to give 3′-(7-difluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile (201 mg, 58%) as a yellow powder: δH (400 MHz, CDCl3) 6.67 (1H, t, J 55) 7.29 (1H, d, J 7), 7.52 (1H, td, J 9 and 1), 7.58-7.74 (5H, m), 7.87 (2H, m), 8.01 (1H, s), 9.12 (1H, d, J 7); m/z (ES+) 347 (M++H).

Sources & evidence

ORD record
ord-762390e6400b4e0588debce229997ed1
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

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