3-Bromo-7-difluoromethylimidazo[1,2-a]pyrimidine → 3'-(7-Difluoromethylimidazo[1,2-alpha]pyrimidin-3-yl)-4'-fluorobiphenyl-2-carbonitrile

HRID 2183897Notes

Reaction equation

HRID 2183897 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.[F:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]2[C:22]([C:27]#[N:28])=[CH:23][CH:24]=[CH:25][CH:26]=2)=[CH:17][C:16]=1B1OC(C)(C)C(C)(C)O1>>[F:12][CH:11]([F:13])[C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:20]3[CH:19]=[C:18]([C:21]4[C:22]([C:27]#[N:28])=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH:17]=[CH:16][C:15]=3[F:14])=[CH:3][N:4]=[C:5]2[N:10]=1

Participants

3

Reactant 2

HCID 180012863-Bromo-7-difluoromethylimidazo[1,2-a]pyrimidineHCID 224735984'-Fluoro-3'-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-biphenyl-2-carbonitrile

Product 1

HCID 102922183'-(7-Difluoromethylimidazo[1,2-alpha]pyrimidin-3-yl)-4'-fluorobiphenyl-2-carbonitrileYield 49%

Procedure

3-Bromo-7-difluoromethylimidazo[1,2-α]pyrimidine (124 mg, 0.50 mmol) was coupled with 4′-fluoro-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-α]pyrimidin-3-yl)-4′-fluorobiphenyl-2-carbonitrile (180 mg, 49%) as a yellow powder: δH (400 MHz, CDCl3) 6.69 (1H, t, J 55), 7.32 (1H, d, J 7), 7.42-7.57 (3H, m), 7.64-7.76 (3H, m), 7.84 (1H, dd, J 8 and 1), 8.13 (1H, d, J 1), 8.79 (1H, dd, J 7 and 2); m/z (ES+) 365 (M++H).

Sources & evidence

ORD record
ord-066e614645b940ae90918ac497ec656c
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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