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

HRID 1180253Notes

Reaction equation

HRID 1180253 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]=[CH:20][C:21]=1[F:22]>>[F:29][C:26]1[CH:25]=[C:24]([C:30]#[N:31])[C:23]([C:18]2[CH:17]=[CH:16][C:21]([F:22])=[C:20]([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:19]=2)=[CH:28][CH:27]=1

Participants

3

Reactant 2

HCID 179648253'-Bromo-4,4'-difluorobiphenyl-2-carbonitrileHCID 444087292-(8-Fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 99787244,4'-Difluoro-3'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-2-carbonitrileYield 6%

Procedure

2-(8-Fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol was coupled to 3′-bromo-4,4′-difluorobiphenyl-2-carbonitrile (prepared in the same way as in Example 2) as described in Example 6 to give 4,4′-difluoro-3′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]biphenyl-2-carbonitrile (trifluoroacetate salt) as an off-white solid (23 mg, 6%); m/z (ES+) 408 [MH+].

Workup

  1. customprepared in the same way as in Example 2)

Sources & evidence

ORD record
ord-d2976ec49186481badc01c37463a8f50
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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