3-bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine → 5,2-Difluoro-5-(7-trifluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile

HRID 2183968Notes

Reaction equation

HRID 2183968 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]2=[N:4][CH:3]=1.CC1(C)COB([C:22]2[CH:23]=[CH:24][C:25]([F:37])=[C:26]([C:28]3[C:29]([C:35]#[N:36])=[CH:30][CH:31]=[C:32]([F:34])[CH:33]=3)[CH:27]=2)OC1>>[F:34][C:32]1[CH:33]=[C:28]([C:26]2[CH:27]=[C:22]([C:2]3[N:6]4[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]4=[N:4][CH:3]=3)[CH:23]=[CH:24][C:25]=2[F:37])[C:29]([C:35]#[N:36])=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 113914623-bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineHCID 116884435'-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-5,2'-difluorobiphenyl-2-carbonitrile

Product 1

HCID 102009755,2-Difluoro-5-(7-trifluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile

Procedure

3-Bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine was coupled with 5′-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)-5,2′-difluorobiphenyl-2-carbonitrile as described in Example 1 to give 5,2′-difluoro-5′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile as an off-white solid: δH (360 MHz, CDCl3) 7.25-7.31 (2H, m), 7.44-7.50 (1H, m), 7.67 (1H, ddd, J 9, 5 and 2), 7.67 (1H, s), 7.69 (1H, s), 7.88 (1H, dd, J 9 and 6), 8.11 (1H, s), 9.05 (1H, d, J 7); m/z (ES+) 401 (M++H).

Sources & evidence

ORD record
ord-6571c13d6b324ac5838d76f434c67188
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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