3'-Bromo-4,2',6'-trifluorobiphenyl-2-carbonitrile → 3'-[8-Fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]-4,2',6'-trifluorobiphenyl-2-carbonitrile

HRID 1180262Notes

Reaction equation

HRID 1180262 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][C:26]([F:29])=[CH:27][CH:28]=2)[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][C:26]([F:29])=[CH:27][CH:28]=4)[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 222401013'-Bromo-4,2',6'-trifluorobiphenyl-2-carbonitrileHCID 444087292-(8-Fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 103650733'-[8-Fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]-4,2',6'-trifluorobiphenyl-2-carbonitrileYield 36.4%

Procedure

2-(8-Fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol (194 mg, 1.0 mmol) and 3′-bromo-4,2′,6′-trifluorobiphenyl-2-carbonitrile (343 mg, 1.1 mmol) were coupled following the procedure in Example 6 to afford 3′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]-4,2′,6′-trifluorobiphenyl-2-carbonitrile (155 mg, 36%) as a white solid: δH (360 MHz, CDCl3) 1.74 (6H, s), 2.07 (1H, s), 7.19-7.26 (2H, m), 7.41-7.49 (1H, m), 7.54-7.65 (3H, m), 7.73 (1H, s), 7.93 (1H, dd, J 7 and 7); m/z (ES+) 426 (100%, [MH]+).

Sources & evidence

ORD record
ord-b47a468104c2441491917cacd0e4916d
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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