4-Fluoro-3-(pyridin-3-yl)benzeneboronic acid → 2-[3-(4-Fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-alpha]pyrimidin-7-yl)-2-methylpropionitrile

HRID 2184036Notes

Reaction equation

HRID 2184036 reaction equation
Br[C:2]1[N:6]2[CH:7]=[CH:8][C:9]([C:11]([CH3:15])([CH3:14])[C:12]#[N:13])=[N:10][C:5]2=[N:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][C:18]=1[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1>>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[N:6]3[CH:7]=[CH:8][C:9]([C:11]([CH3:15])([CH3:14])[C:12]#[N:13])=[N:10][C:5]3=[N:4][CH:3]=2)=[CH:19][C:18]=1[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 224735734-Fluoro-3-(pyridin-3-yl)benzeneboronic acidHCID 697082082-(3-Bromoimidazo[1,2-alpha]pyrimidin-7-yl)-2-methylpropionitrile

Product 1

HCID 101329702-[3-(4-Fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-alpha]pyrimidin-7-yl)-2-methylpropionitrile

Procedure

2-(3-Bromoimidazo[1,2-α]pyrimidin-7-yl)-2-methylpropionitrile and 4-fluoro-3-(pyridin-3-yl)benzeneboronic acid were coupled following the procedure in Example 65 to give 2-[3-(4-fluoro-3-(pyridin-3-yl)phenyl)imidazo[1,2-α]pyrimidin-7-yl)-2-methylpropionitrile as a white solid: δH (360 MHz, CDCl3) 1.86 (6H, s), 7.32 (1H, d, J 7), 7.38-7.45 (2H, m), 7.53-7.62 (2H, m), 7.86-7.97 (1H, m), 7.91 (1H, d, J 3), 8.62 (1H, d, J 7), 8.67 (1H, dd, J 8 and 3), 8.84 (1H, s); m/z (ES+) 358 (M++H).

Sources & evidence

ORD record
ord-286094065aa84e7281330a20875c2d98
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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