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

HRID 2183920Notes

Reaction equation

HRID 2183920 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.[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25](B(O)O)[C:24]=1[F:32])#[N:16]>>[F:32][C:24]1[C:25]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]([F:14])([F:13])[F:12])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:26][CH:27]=[CH:28][C:23]=1[C:18]1[C:17]([C:15]#[N:16])=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

3

Reactant 2

HCID 113914623-Bromo-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineHCID 11644397(2'-Cyano-2-fluoro-[1,1'-biphenyl]-3-yl)boronic acid

Product 1

HCID 101344802-Fluoro-3-(7-trifluoromethylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrileYield 18%

Procedure

3-Bromo-7-trifluoromethylimidazo[1,2-α]pyrimidine was coupled with 2′-cyano-2-fluorobiphenyl-3-boronic acid as described in Example 1 to give 2′-fluoro-3′-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)biphenyl-2-carbonitrile as an off-white solid (70 mg, 18%): δH (400 MHz, DMSO) 7.60-7.64 (2H, m), 7.70 (1H, d, J 1), 7.76 (1H, d, J 2), 7.83 (1H, s), 7.87-7.91 (2H, m), 8.05 (1H, dd, J 7 and 1), 8.35 (1H, s), 9.13 (1H, dd, J 7 and 3); m/z (ES+) 383 (M++H).

Sources & evidence

ORD record
ord-e0cb65624d9143f9a82dac41de7ac1a8
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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