5'-Bromo-2',4-difluoro-[1,1'-biphenyl]-2-carbonitrile → 4,2'-Difluoro-5'-(8-fluoro-7-trifluoromethylimidazo[1,2-alpha]pyridin-3-yl)-biphenyl-2-carbonitrile

HRID 1180316Notes

Reaction equation

HRID 1180316 reaction equation
[F:1][C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]([F:11])([F:10])[F:9].Br[C:16]1[CH:17]=[CH:18][C:19]([F:31])=[C:20]([C:22]2[C:23]([C:29]#[N:30])=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH:21]=1>>[F:28][C:25]1[CH:24]=[C:23]([C:29]#[N:30])[C:22]([C:20]2[CH:21]=[C:16]([C:12]3[N:4]4[CH:5]=[CH:6][C:7]([C:8]([F:9])([F:10])[F:11])=[C:2]([F:1])[C:3]4=[N:14][CH:13]=3)[CH:17]=[CH:18][C:19]=2[F:31])=[CH:27][CH:26]=1

Participants

3

Reactant 2

HCID 114151595'-Bromo-2',4-difluoro-[1,1'-biphenyl]-2-carbonitrileHCID 674863248-Fluoro-7-(trifluoromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 102513824,2'-Difluoro-5'-(8-fluoro-7-trifluoromethylimidazo[1,2-alpha]pyridin-3-yl)-biphenyl-2-carbonitrileYield 45%

Procedure

8-Fluoro-7-trifluoromethylimidazo[1,2-α]pyridine (102 mg, 0.5 mmol) and 5′-bromo-4,2′-difluorobiphenyl-2-carbonitrile (221 mg, 0.75 mmol) were coupled following the procedure given in Example 6 to afford 4,2′-difluoro-5′-(8-fluoro-7-trifluoromethylimidazo[1,2-α]pyridin-3-yl)-biphenyl-2-carbonitrile (93 mg, 45%) as an off-white solid: δH (360 MHz, CDCl3) 7.00 (1H, dd, J 7 and 6), 7.40-7.47 (2H, m), 7.55 (1H, dd, J 8 and 3), 7.57-7.65 (3H, m), 7.86 (1H, s), 8.34 (1H, d, J 7); m/z (ES+) 418 (100%, [MH]+).

Sources & evidence

ORD record
ord-2389bafabe384ab0848525adee6e1f4c
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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