3'-Bromo-6,2',6'-trifluorobiphenyl-2-carbonitrile → 3'-[8-Fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]-6,2',6'-trifluorobiphenyl-2-carbonitrile

HRID 1180252Notes

Reaction equation

HRID 1180252 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[C:17]([F:32])=[C:18]([C:23]2[C:24]([C:30]#[N:31])=[CH:25][CH:26]=[CH:27][C:28]=2[F:29])[C:19]([F:22])=[CH:20][CH:21]=1>>[F:1][C:2]1[C:3]2[N:4]([C:12]([C:20]3[C:19]([F:22])=[C:18]([C:23]4[C:24]([C:30]#[N:31])=[CH:25][CH:26]=[CH:27][C:28]=4[F:29])[C:17]([F:32])=[CH:16][CH:21]=3)=[CH:13][N:14]=2)[CH:5]=[CH:6][C:7]=1[C:8]([OH:11])([CH3:10])[CH3:9]

Participants

3

Reactant 2

HCID 222401023'-Bromo-6,2',6'-trifluorobiphenyl-2-carbonitrileHCID 444087292-(8-Fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 104550743'-[8-Fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]-6,2',6'-trifluorobiphenyl-2-carbonitrileYield 10%

Procedure

2-(8-Fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol was coupled to 3′-bromo-6,2′,6′-trifluorobiphenyl-2-carbonitrile as described in Example 6 to give 3′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]-6,2′,6′-trifluorobiphenyl-2-carbonitrile as an off-white solid (17 mg, 10%): δH (400 MHz, d6-DMSO) 1.58 (6H, s), 5.56 (1H, s), 7.23 (1H, t, J 7), 7.61 (1H, t, J 8), 7.84-7.87 (3H, m), 7.95-8.01 (2H, m), 8.08 (1H, dd, J 7 and 3); m/z (ES+) 426 [MH+]

Sources & evidence

ORD record
ord-9196f0a54f204b8bbf63e2cdd582f20c
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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