Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 69708303, compound

HRID 2183953Notes

Reaction equation

HRID 2183953 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:15])=[C:6]([C:8]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=2)[CH:7]=1.C([Sn](CCCC)(CCCC)[C:21]1[N:25]2[CH:26]=[CH:27][C:28]([C:30]([F:33])([F:32])[F:31])=[N:29][C:24]2=[N:23][CH:22]=1)CCC>>[F:15][C:5]1[CH:4]=[CH:3][C:2]([C:21]2[N:25]3[CH:26]=[CH:27][C:28]([C:30]([F:31])([F:32])[F:33])=[N:29][C:24]3=[N:23][CH:22]=2)=[CH:7][C:6]=1[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][N:9]=1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 22473563HCID 22473563, compound

Product 1

HCID 69708303HCID 69708303, compound

Procedure

2-(5-Bromo-2-fluorophenyl)-4-methylpyridine was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine by the method of Example 32. Purification by chromatography on silica gel eluting with dichloromethane containing 1% methanol, then crystallisation from ethyl acetate/isohexane, gave 3-[4-fluoro-3-(4-methylpyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as a yellow powder: δH (400 MHz, CDCl3) 8.87 (1H, d, J 7), 8.58 (1H, d, J 5), 8.24 (1H, dd, J 7 and 2), 8.12 (1H, s), 7.71 (1H, s), 7.53-7.58 (1H, m), 7.38 (1H, dd, J 11 and 8), 7.26 (1H, d, J 7), 7.16 (1H, d, J 5), 2.46 (3H, s); m/z (ES+) 373 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 1% methanol
  2. customcrystallisation from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-3d4ddc9cc8fa412baf6fba580473f4f2
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

Loading…