HCID 11336372, compound → 4,2'-Difluoro-5'-(8-fluoroimidazo[1,2-alpha]pyridin-3-yl)biphenyl-2-carbonitrile

HRID 1180242Notes

Reaction equation

HRID 1180242 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][CH:9]=[C:10]([F:11])[C:5]2=[N:4][CH:3]=1.[F:12][C:13]1[CH:14]=[C:15]([C:34]#[N:35])[C:16]([C:19]2[CH:24]=[C:23](B3OCC(C)(C)CO3)[CH:22]=[CH:21][C:20]=2[F:33])=[CH:17][CH:18]=1>>[F:12][C:13]1[CH:14]=[C:15]([C:34]#[N:35])[C:16]([C:19]2[CH:24]=[C:23]([C:2]3[N:6]4[CH:7]=[CH:8][CH:9]=[C:10]([F:11])[C:5]4=[N:4][CH:3]=3)[CH:22]=[CH:21][C:20]=2[F:33])=[CH:17][CH:18]=1

Participants

3

Reactant 2

HCID 11336372HCID 11336372, compoundHCID 341764763-Bromo-8-fluoroimidazo[1,2-a]pyridine

Product 1

HCID 100207064,2'-Difluoro-5'-(8-fluoroimidazo[1,2-alpha]pyridin-3-yl)biphenyl-2-carbonitrileYield 55%

Procedure

3-Bromo-8-fluoroimidazo[1,2-α]pyridine (0.10 g, 0.47 mmol) and 4,2′-difluoro-5′-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)biphenyl-2-carbonitrile (0.28 g, 0.83 mmol) were coupled following the procedure in Example 1 to afford 4,2′-difluoro-5′-(8-fluoroimidazo[1,2-α]pyridin-3-yl)biphenyl-2-carbonitrile as a white amorphous solid (90 mg, 55%): δH (360 MHz, CDCl3) 6.79-6.83 (1H, m), 6.94 (1H, dd, J 8 and 8), 7.73-7.46 (2H, m), 7.53-7.65 (4H, m), 7.73 (1H, s), 8.25 (1H, d, J 7); m/z (ES+) 350 (M++H).

Sources & evidence

ORD record
ord-6a85c4c5fc1d4140ba34a5373114605b
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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