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

HRID 1180249Notes

Reaction equation

HRID 1180249 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[C:23]([C:29]#[N:30])=[CH:24][CH:25]=[C:26]([F:28])[CH:27]=2)[CH:21]=1>>[F:28][C:26]1[CH:27]=[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])[C:23]([C:29]#[N:30])=[CH:24][CH:25]=1

Participants

3

Reactant 2

HCID 117020585'-Bromo-5,2'-difluorobiphenyl-2-carbonitrileHCID 444087292-(8-Fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 104091125,2'-Difluoro-5'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-2-carbonitrileYield 43%

Procedure

2-(8-Fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol was coupled to 5′-bromo-5,2′-difluorobiphenyl-2-carbonitrile (prepared as described in WO 02/38568) as described in Example 6 to give 5,2′-difluoro-5′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]biphenyl-2-carbonitrile as a white solid (90 mg, 43%): δH (360 MHz, d6-DMSO) 1.58 (6H, s), 7.21 (1H, m), 7.54-7.65 (2H, m), 7.77 (1H, dd, J 10 and 3), 7.84-7.89 (3H, m), 8.15 (1H, dd, J 9 and 6), 8.49 (1H, d, J 7); m/z (ES+) 408 [MH+].

Sources & evidence

ORD record
ord-93e132c3e161432387303700d9dd3a5e
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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