2′-Fluoro-5′-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)[1,1′-biphenyl]-2-carbonitrile → 5'-(7-Difluoromethylimidazo[1,2-alpha]pyrimidin-3-yl)-2'-fluorobiphenyl-2-carbonitrile
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](B2OC(C)(C)C(C)(C)O2)=[CH:17][C:16]=1[C:30]1[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=1>>[F:12][CH:11]([F:13])[C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:18]3[CH:19]=[CH:20][C:15]([F:14])=[C:16]([C:30]4[C:31]([C:36]#[N:37])=[CH:32][CH:33]=[CH:34][CH:35]=4)[CH:17]=3)=[CH:3][N:4]=[C:5]2[N:10]=1Participants
3
Procedure
3-Bromo-7-difluoromethylimidazo[1,2-α]pyrimidine (248 mg, 1.00 mmol) was coupled with 2′-fluoro-5′-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)biphenyl-2-carbonitrile as described in Example 1 to give 5′-(7-difluoromethylimidazo[1,2-α]pyrimidin-3-yl)-2′-fluorobiphenyl-2-carbonitrile (180 mg, 49%) as a yellow powder: δH (400 MHz, CDCl3) 6.66 (1H, t, J 55), 7.29 (1H, d, J 7), 7.44 (1H, t, J 9), 7.54-7.74 (5H, m), 7.87 (1H, dd, J 8 and 1), 8.02 (1H, s), 9.00 (1H, d, J 7); m/z (ES+) 365 (M++H).