3-Acetylphenylboronic acid → 1-{2'-Fluoro-5'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-3-yl}ethanone

HRID 1180272Notes

Reaction equation

HRID 1180272 reaction equation
Cl[C:2]1[CH:3]=[C:4]([C:9]2[N:13]3[CH:14]=[CH:15][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[C:17]([F:18])[C:12]3=[N:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[F:8].[C:23]([C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1)(=[O:25])[CH3:24]>>[F:8][C:7]1[CH:6]=[CH:5][C:4]([C:9]2[N:13]3[CH:14]=[CH:15][C:16]([C:19]([OH:22])([CH3:21])[CH3:20])=[C:17]([F:18])[C:12]3=[N:11][CH:10]=2)=[CH:3][C:2]=1[C:30]1[CH:29]=[CH:28][CH:27]=[C:26]([C:23](=[O:25])[CH3:24])[CH:31]=1

Participants

3

Reactant 2

HCID 27343103-Acetylphenylboronic acidHCID 674866802-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-alpha]pyridin-7-yl]propan-2-ol

Product 1

HCID 104314391-{2'-Fluoro-5'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-3-yl}ethanoneYield 11%

Procedure

2-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]-propan-2-ol and 3-acetylbenzeneboronic acid were coupled in the same way as in Example 30 to give 1-{2′-fluoro-5′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]biphenyl-3-yl}ethanone as an off-white solid (14 mg, 11%): m/z (ES+) 407 [MH+].

Sources & evidence

ORD record
ord-923f271e56c9422c916d19d6b167be89
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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