Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 69708694, compound

HRID 2184045Notes

Reaction equation

HRID 2184045 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([F:16])=[C:6]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][N:9]=2)[CH:7]=1.C([Sn](CCCC)(CCCC)[C:22]1[N:26]2[CH:27]=[CH:28][C:29]([C:31]([F:34])([F:33])[F:32])=[N:30][C:25]2=[N:24][CH:23]=1)CCC>>[F:16][C:5]1[CH:4]=[CH:3][C:2]([C:22]2[N:26]3[CH:27]=[CH:28][C:29]([C:31]([F:32])([F:33])[F:34])=[N:30][C:25]3=[N:24][CH:23]=2)=[CH:7][C:6]=1[C:8]1[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[CH:10][N:9]=1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 22473589HCID 22473589, compound

Product 1

HCID 69708694HCID 69708694, compound

Procedure

2-(5-Bromo-2-fluorophenyl)-4-methoxypyridine (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-(4-methoxypyridin-2-yl)phenyl]-7-trifluoromethylimidazo[1,2-α]pyrimidine as a yellow solid: δH (400 MHz, CDCl3) 3.93 (3H, s), 6.86 (1H, dd, J 5 and 2), 7.26 (1H, d, J 7), 7.38 (1H, dd, J 11 and 9), 7.42 (1H, s), 7.54-7.58 (1H, m), 8.12 (1H, s), 8.26 (1H, dd, J 7 and 2), 8.54 (1H, d, J 5), 8.86 (1H, d, J 7); m/z (ES+) 388 (M++H).

Workup

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

Sources & evidence

ORD record
ord-8cf5d71af0d04b42b0f62898f11e15fc
Source dataset
uspto-grants-2005_05
Patent number
US06900215B2

Reaction notes

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