(4-Fluoro-2-methylphenyl)boronic acid → 2-[3-(2,4'-Difluoro-2'-methylbiphenyl-5-yl)-8-fluoroimidazo[1,2-alpha]pyridin-7-yl]propan-2-ol

HRID 1180270Notes

Reaction equation

HRID 1180270 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].[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[C:26]([CH3:33])[CH:25]=1>>[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:27]1[CH:28]=[CH:29][C:24]([F:23])=[CH:25][C:26]=1[CH3:33]

Participants

3

Reactant 2

HCID 2734665(4-Fluoro-2-methylphenyl)boronic acidHCID 674866802-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-alpha]pyridin-7-yl]propan-2-ol

Product 1

HCID 100921312-[3-(2,4'-Difluoro-2'-methylbiphenyl-5-yl)-8-fluoroimidazo[1,2-alpha]pyridin-7-yl]propan-2-olYield 58.2%

Procedure

2-[3-(3-Chloro-4-fluorophenyl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]-propan-2-ol (100 mg, 0.36 mmol) and 4-fluoro-2-methylphenylboronic acid (83 mg, 0.54 mmol) were coupled using the procedure in Example 30 to afford 2-[3-(2,4′-difluoro-2′-methylbiphenyl-5-yl)-8-fluoroimidazo[1,2-α]pyridin-7-yl]propan-2-ol (83 mg, 58%) as a white solid: δH (360 MHz, CDCl3) 1.74 (6H, s), 2.04 (1H, s), 2.26 (3H, s), 6.95-7.05 (2H, m), 7.15-7.33 (3H, m), 7.40 (1H, dd, J 7 and 2), 7.51-7.56 (1H, m), 7.69 (1H, s), 8.06 (1H, d, J 7); m/z (ES+) 397 (100%, [MH]+).

Sources & evidence

ORD record
ord-10dd4a8cd77e45199cdecd8b7512973e
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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