5-Fluoro-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile → 4,2'-Difluoro-5'-(5-methyl-4-oxo-4,5-dihydroimidazo[4,5-c]pyridin-1-yl)biphenyl-2-carbonitrile

HRID 2180038Notes

Reaction equation

HRID 2180038 reaction equation
Br[C:2]1[CH:3]=[C:4]([N:9]2[C:17]3[CH:16]=[CH:15][N:14]([CH3:18])[C:13](=[O:19])[C:12]=3[N:11]=[CH:10]2)[CH:5]=[CH:6][C:7]=1[F:8].[F:20][C:21]1[CH:22]=[CH:23][C:24](B2OC(C)(C)C(C)(C)O2)=[C:25]([CH:28]=1)[C:26]#[N:27]>>[F:20][C:21]1[CH:28]=[C:25]([C:26]#[N:27])[C:24]([C:2]2[CH:3]=[C:4]([N:9]3[C:17]4[CH:16]=[CH:15][N:14]([CH3:18])[C:13](=[O:19])[C:12]=4[N:11]=[CH:10]3)[CH:5]=[CH:6][C:7]=2[F:8])=[CH:23][CH:22]=1

Participants

3

Reactant 2

HCID 221807905-Fluoro-2-(tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrileHCID 224902931-(3-Bromo-4-fluorophenyl)-5-methyl-1,5-dihydroimidazo[4,5-c]pyridin-4-one

Product 1

HCID 224902964,2'-Difluoro-5'-(5-methyl-4-oxo-4,5-dihydroimidazo[4,5-c]pyridin-1-yl)biphenyl-2-carbonitrileYield 55%

Procedure

1-(3-Bromo-4-fluorophenyl)-5-methyl-1,5-dihydroimidazo[4,5-c]pyridin-4-one was coupled to 5-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile, in the same way as in Example 1, to give 4,2′-difluoro-5′-(5-methyl-4-oxo-4,5-dihydroimidazo[4,5-c]pyridin-1-yl)biphenyl-2-carbonitrile as an off-white solid (360 mg, 55%): δH (400 MHz, d6-DMSO) 3.54 (3H, s), 6.67 (1H, d, J 7), 7.61 (1H, d, J 7), 7.69 (1H, t, J 9), 7.75-7.87 (4H, m), 8.09 (1H, dd, J 9 and 3), 8.38 (1H, s); m/z (ES+, 363 [MH+].

Sources & evidence

ORD record
ord-3ab2d8ea9cfd4e05b570f95907495ecf
Source dataset
uspto-grants-2005_05
Patent number
US06887885B2

Reaction notes

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