3'-Bromo-4,5'-difluorobiphenyl-2-carbonitrile → 4,3'-Difluoro-5'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]-biphenyl-2-carbonitrile

HRID 1180259Notes

Reaction equation

HRID 1180259 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]([OH:11])([CH3:10])[CH3:9].Br[C:16]1[CH:17]=[C:18]([C:23]2[C:24]([C:30]#[N:31])=[CH:25][C:26]([F:29])=[CH:27][CH:28]=2)[CH:19]=[C:20]([F:22])[CH:21]=1>>[F:29][C:26]1[CH:25]=[C:24]([C:30]#[N:31])[C:23]([C:18]2[CH:17]=[C:16]([C:12]3[N:4]4[CH:5]=[CH:6][C:7]([C:8]([OH:11])([CH3:10])[CH3:9])=[C:2]([F:1])[C:3]4=[N:14][CH:13]=3)[CH:21]=[C:20]([F:22])[CH:19]=2)=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 179648413'-Bromo-4,5'-difluorobiphenyl-2-carbonitrileHCID 444087292-(8-Fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 104315084,3'-Difluoro-5'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]-biphenyl-2-carbonitrileYield 20.5%

Procedure

2-(8-Fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol (58 mg, 0.3 mmol) and 3′-bromo-4,5′-difluorobiphenyl-2-carbonitrile (106 mg, 0.36 mmol) were coupled following the procedure in Example 6 to afford 4,3′-difluoro-5′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]-biphenyl-2-carbonitrile (25 mg, 20%) as a white solid: δH (500 Ndz, CDCl3) 1.74 (6H, s), 2.07 (1H, s), 7.22-7.26 (2H, m), 7.35 (1H, d, J 9), 7.39-7.45 (1H, m), 7.51-7.57 (3H, m), 7.76 (1H, s), 8.35 (1H, d, J 7); m/z (ES+) 408 (100%, [MH]+).

Sources & evidence

ORD record
ord-ba3e48e6ae1c4c7a9dc67de5b93256a2
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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