3-(2-Chloropyrimidin-4-yl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidine → 5-Fluoro-2-{4-[7-trifluoromethylimidazo[1,2-alpha]pyrimidin-3-yl]pyrimidin-2-yl}benzonitrile

HRID 1796055Notes

Reaction equation

HRID 1796055 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[N:12]3[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]3=[N:10][CH:9]=2)[CH:5]=[CH:4][N:3]=1.[F:21][C:22]1[CH:23]=[CH:24][C:25](C2C=CC=C(C3N4C=CC(C(O)(C)C)=NC4=NC=3)N=2)=[C:26]([CH:29]=1)[C:27]#[N:28]>>[F:21][C:22]1[CH:23]=[CH:24][C:25]([C:2]2[N:7]=[C:6]([C:8]3[N:12]4[CH:13]=[CH:14][C:15]([C:17]([F:20])([F:19])[F:18])=[N:16][C:11]4=[N:10][CH:9]=3)[CH:5]=[CH:4][N:3]=2)=[C:26]([CH:29]=1)[C:27]#[N:28]

Participants

3

Reactant 2

HCID 98574753-(2-Chloropyrimidin-4-yl)-7-(trifluoromethyl)imidazo[1,2-a]pyrimidineHCID 102706675-Fluoro-2-{6-[7-(1-hydroxy-1-methylethyl)imidazo[1,2-alpha]pyrimidin-3-yl]pyridin-2-yl}benzonitrile

Product 1

HCID 102000205-Fluoro-2-{4-[7-trifluoromethylimidazo[1,2-alpha]pyrimidin-3-yl]pyrimidin-2-yl}benzonitrile

Procedure

3-(2-Chloropyrimidin-4-yl)-7-trifluoromethylimidazo[1,2-α]pyrimidine was coupled to 5-fluoro-2-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)benzonitrile (synthesised as in Example 22) by the method of Example 1 to afford 5-fluoro-2-{4-[7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl]pyrimidin-2-yl}benzonitrile as a white solid: δH (400 MHz, CDCl3) 7.48-7.53 (2H, m), 7.63 (1H, dd, J 2.5, 8.0), 7.78 (1H, d, J 5.5), 8.39 (1H, dd, J 5.5, 9.0), 8.74 (1H, s), 8.95 (1H, d, J 5.5), 10.67 (1H, d, J 6.7); m/z (ES+) 385 (M++H).

Sources & evidence

ORD record
ord-18b1bb26460340dcbae59f081e2d2ab4
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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