(3-Chloro-2-methylphenyl)boronic acid → 2-[3-(3'-Chloro-2-fluoro-2'-methylbiphenyl-5-yl)-8-fluoroimidazo[1,2-alpha]pyridin-7-yl]propan-2-ol

HRID 1180286Notes

Reaction equation

HRID 1180286 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].[Cl:23][C:24]1[C:25]([CH3:33])=[C:26](B(O)O)[CH:27]=[CH:28][CH:29]=1>>[Cl:23][C:24]1[C:25]([CH3:33])=[C:26]([C:2]2[CH:3]=[C:4]([C:9]3[N:13]4[CH:14]=[CH:15][C:16]([C:19]([OH:22])([CH3:20])[CH3:21])=[C:17]([F:18])[C:12]4=[N:11][CH:10]=3)[CH:5]=[CH:6][C:7]=2[F:8])[CH:27]=[CH:28][CH:29]=1

Participants

3

Reactant 2

HCID 3744103(3-Chloro-2-methylphenyl)boronic acidHCID 674866802-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-alpha]pyridin-7-yl]propan-2-ol

Product 1

HCID 103870052-[3-(3'-Chloro-2-fluoro-2'-methylbiphenyl-5-yl)-8-fluoroimidazo[1,2-alpha]pyridin-7-yl]propan-2-olYield 4%

Procedure

2-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]-propan-2-ol and 3-chloro-2-methylbenzeneboronic acid were coupled in the same way as in Example 30 to give 2-[3-(3′-chloro-2-fluoro-2′-methylbiphenyl-5-yl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]propan-2-ol as an off-white solid (5 mg, 4%): m/z (ES+) 413 [MH+].

Sources & evidence

ORD record
ord-e2ffa747b78a4befa8d449e5353fea85
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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