2-Bromo-5-fluorobenzonitrile → 4-Fluoro-3'-(7-methylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile

HRID 478245Notes

Reaction equation

HRID 478245 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13](B4OC(C)(C)C(C)(C)O4)[CH:12]=3)=[CH:9][N:10]=[C:4]2[N:3]=1.Br[C:27]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][C:28]=1[C:29]#[N:30]>>[F:35][C:32]1[CH:31]=[C:28]([C:29]#[N:30])[C:27]([C:13]2[CH:14]=[CH:15][CH:16]=[C:11]([C:8]3[N:5]4[CH:6]=[CH:7][C:2]([CH3:1])=[N:3][C:4]4=[N:10][CH:9]=3)[CH:12]=2)=[CH:34][CH:33]=1

Participants

3

Reactant 2

HCID 936542-Bromo-5-fluorobenzonitrileHCID 180012787-Methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]imidazo[1,2-a]pyrimidine

Product 1

HCID 101314624-Fluoro-3'-(7-methylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrileYield 43.1%

Procedure

7-Methyl-3-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)phenyl]-imidazo[1,2-a]pyrimidine (0.2 g, 0.6 mmol) was coupled to 2-bromo-5-fluorobenzonitrile (179 mg, 0.9 mmol) as described in Example 26 to give 4-fluoro-3′-(7-methylimidazo[1,2-a]pyrimidin-3-yl)biphenyl-2-carbonitrile as a white solid (85 mg): δH (400 MHz, CDCl3) 2.67 (3H, s), 6.83 (1H, d, J 7), 7.20 (1H, dt, J 8.9 and 3), 7.50-7.70 (6H, m), 7.84 (1H, s), 8.76 (1H, d, J 7); m/z (ES+) 329 (M++H).

Sources & evidence

ORD record
ord-8b8a358f64c7437984208d8197ee9424
Source dataset
uspto-grants-2003_11
Patent number
US06642229B2

Reaction notes

Loading…