5'-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-3,2'-difluorobiphenyl-2-carbonitrile → 3,2'-Difluoro-5'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-2-carbonitrile

HRID 1180239Notes

Reaction equation

HRID 1180239 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])=[C:10]([F:11])[C:5]2=[N:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[C:27](B3OCC(C)(C)CO3)[CH:26]=[CH:25][C:24]=2[F:37])[C:18]=1[C:38]#[N:39]>>[F:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([C:23]2[CH:28]=[C:27]([C:2]3[N:6]4[CH:7]=[CH:8][C:9]([C:12]([OH:15])([CH3:14])[CH3:13])=[C:10]([F:11])[C:5]4=[N:4][CH:3]=3)[CH:26]=[CH:25][C:24]=2[F:37])[C:18]=1[C:38]#[N:39]

Participants

3

Reactant 2

HCID 115153815'-(5,5-Dimethyl-[1,3,2]dioxaborinan-2-yl)-3,2'-difluorobiphenyl-2-carbonitrileHCID 674869102-(3-Bromo-8-fluoroimidazo[1,2-a]pyridin-7-yl)propan-2-ol

Product 1

HCID 103866753,2'-Difluoro-5'-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyridin-3-yl]biphenyl-2-carbonitrileYield 75%

Procedure

3-Bromo-8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridine (0.10 g, 0.36 mmol) and 3,2′-difluoro-5′-(5,5-dimethyl-[1,3,2]dioxaborinan-2-yl)biphenyl-2-carbonitrile (0.16 g, 0.47 mmol) were coupled following the procedure in Example 1 to afford 3,2′-difluoro-5′-[8-fluoro-7-(1-hydroxy-1-methylethyl)imidazo[1,2-α]pyridin-3-yl]biphenyl-2-carbonitrile as a white amorphous solid (110 mg, 74%): δH (360 MHz, CDCl3) 1.73 (6H, s), 2.10 (1H, s), 7.21 (1H, dd, J 7 and 7), 7.30 (1H, dd, J 8 and 8), 7.38-7.44 (2H, m), 7.61-7.72 (4H, m), 8.23 (1H, d, J 7); m/z (ES+) 408 (M++H).

Sources & evidence

ORD record
ord-455f7ea345d14e02a88b7a4f063227cd
Source dataset
uspto-grants-2007_10
Patent number
US07279580B2

Reaction notes

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