Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 9969028, compound

HRID 2184047Notes

Reaction equation

HRID 2184047 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:13])=[C:6]([C:8]2[S:9][CH:10]=[CH:11][N:12]=2)[CH:7]=1.C([Sn](CCCC)(CCCC)[C:19]1[N:23]2[CH:24]=[CH:25][C:26]([C:28]([F:31])([F:30])[F:29])=[N:27][C:22]2=[N:21][CH:20]=1)CCC>>[F:13][C:5]1[CH:4]=[CH:3][C:2]([C:19]2[N:23]3[CH:24]=[CH:25][C:26]([C:28]([F:29])([F:30])[F:31])=[N:27][C:22]3=[N:21][CH:20]=2)=[CH:7][C:6]=1[C:8]1[S:9][CH:10]=[CH:11][N:12]=1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 22473574HCID 22473574, compound

Product 1

HCID 9969028HCID 9969028, compound

Procedure

2-(5-Bromo-2-fluorophenyl)thiazole (50 mg, 0.2 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (0.3 mmol) by the method of Example 32. Purification by chromatography on silica gel eluting with dichloromethane containing 1% methanol gave 3-[4-fluoro-3-(thiazol-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as a yellow solid: δH (400 MHz, CDCl3) 7.29 (1H, d, J 7), 7.44 (1H, dd, J 11 and 9), 7.56-7.62 (2H, m), 7.97 (1H, dd, J 3 and 2), 8.15 (1H, s), 8.57 (1H, dd, J 7 and 2), 8.86 (1H, d, J 7); m/z (ES+) 364 (M++H).

Workup

  1. customPurification by chromatography on silica gel eluting with dichloromethane containing 1% methanol

Sources & evidence

ORD record
ord-903e16fa41684192bfde77afebfc77ce
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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