Pyridine,4-(5-bromo-2-fluorophenyl)-3,5-difluoro- → 2-{3-[3-(3,5-Difluoropyridin-4-yl)-4-fluorophenyl]-8-fluoroimidazo[1,2-alpha]pyridin-7-yl}propan-2-ol

HRID 1180248Notes

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

Participants

Reactant 2

HCID 17964846Pyridine,4-(5-bromo-2-fluorophenyl)-3,5-difluoro-

HCID 444087292-(8-Fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 100924332-{3-[3-(3,5-Difluoropyridin-4-yl)-4-fluorophenyl]-8-fluoroimidazo[1,2-alpha]pyridin-7-yl}propan-2-olYield 40%

Procedure

2-(8-Fluoroimidazo[1,2-α]pyridin-7-yl)propan-2-ol was coupled to 4-(5-bromo-2-fluorophenyl)-3,5-difluoropyridine as described in Example 6 to give 2-{3-[3-(3,5-difluoropyridin-4-yl)-4-fluorophenyl]-8-fluoroimidazo[1,2-α]pyridin-7-yl}propan-2-ol as an off-white solid (80 mg, 40%): δH (360 MHz, d6-DMSO) 1.57 (6H, s), 7.22 (1H, t, J 7), 7.66 (1H, t, J 9), 7.83 (1H, s), 7.94 (2H, dd, J 6 and 2), 8.37 (1H, d, J 7), 8.75 (2H, s); m/z (ES+) 402 [MH+].

Sources & evidence

ORD record: ord-c912e91b73d0485b95b6d8e06fdae54c
Source dataset: uspto-grants-2007_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07279580B2

Reaction notes

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