HCID 11336372, compound → 5'-(7-Chloro-8-fluoroimidazo[1,2-alpha]pyridin-3-yl)-4,2'-difluorobiphenyl-2-carbonitrile

HRID 1180243Notes

Reaction equation

HRID 1180243 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([Cl:12])=[C:10]([F:11])[C:5]2=[N:4][CH:3]=1.[F:13][C:14]1[CH:15]=[C:16]([C:35]#[N:36])[C:17]([C:20]2[CH:25]=[C:24](B3OCC(C)(C)CO3)[CH:23]=[CH:22][C:21]=2[F:34])=[CH:18][CH:19]=1>>[Cl:12][C:9]1[CH:8]=[CH:7][N:6]2[C:2]([C:24]3[CH:23]=[CH:22][C:21]([F:34])=[C:20]([C:17]4[C:16]([C:35]#[N:36])=[CH:15][C:14]([F:13])=[CH:19][CH:18]=4)[CH:25]=3)=[CH:3][N:4]=[C:5]2[C:10]=1[F:11]

Participants

3

Reactant 2

HCID 11336372HCID 11336372, compoundHCID 695617863-Bromo-7-chloro-8-fluoroimidazo[1,2-a]pyridine

Product 1

HCID 104300665'-(7-Chloro-8-fluoroimidazo[1,2-alpha]pyridin-3-yl)-4,2'-difluorobiphenyl-2-carbonitrileYield 71%

Procedure

3-Bromo-7-chloro-8-fluoroimidazo[1,2-α]pyridine (45 mg, 0.18 mmol) was coupled with 4,2′-difluoro-5′-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)biphenyl-2-carbonitrile (49 mg, 0.19 mmol), as described in Example 1, to afford 5′-(7-chloro-8-fluoroimidazo[1,2-α]pyridin-3-yl)-4,2′-difluorobiphenyl-2-carbonitrile as a white amorphous solid (49 mg, 71%): δH (360 MHz, CDCl3) 6.86 (1H, dd, J 7 and 7), 7.35-7.44 (2H, m), 7.58-7.64 (4H, m), 7.71 (1H, s), 8.20 (1H, d, J 7); m/z (ES+) 384 (100%, [MH]+).

Sources & evidence

ORD record
ord-28f710e0b5814d54be18a1bc31dbec1b
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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