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

HRID 1180254Notes

Reaction equation

HRID 1180254 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]=[CH:18][C:19]([F:31])=[C:20]([C:22]2[CH:27]=[CH:26][C:25]([C:28]#[N:29])=[C:24]([Cl:30])[CH:23]=2)[CH:21]=1>>[Cl:30][C:24]1[CH:23]=[C:22]([C:20]2[CH:21]=[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:17]=[CH:18][C:19]=2[F:31])[CH:27]=[CH:26][C:25]=1[C:28]#[N:29]

Participants

3

Reactant 2

HCID 179648405'-Bromo-3-chloro-2'-fluorobiphenyl-4-carbonitrileHCID 444087292-(8-Fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 100479453-Chloro-2'-fluoro-5'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-4-carbonitrileYield 7%

Procedure

2-(8-Fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol and 5′-bromo-3-chloro-2′-fluorobiphenyl-4-carbonitrile were coupled in the same way as in Example 6 to give 3-chloro-2′-fluoro-5′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]biphenyl-4-carbonitrile as an off-white solid (20 mg, 7%): δH (400 MHz, d6-DMSO) 1.59 (6H, s), 7.33 (1H, t, J 7), 7.63 (1H, dd, J 11 and 9), 7.80-7.89 (2H, m), 7.96 (1H, dd, J 7 and 2), 8.03 (1H, s), 8.11-8.14 (2H, m), 8.53 (1H, d, J 7); m/z (ES+) 424 [MH+].

Sources & evidence

ORD record
ord-167b1bee43764332be6190222bdad098
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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