Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → 3-(6-Cyclopentylpyridin-2-yl)-7-trifluoromethylimidazo[1,2-alpha]pyrimidine

HRID 1796021Notes

Reaction equation

HRID 1796021 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:8]2[CH2:12][CH2:11][CH2:10][CH2:9]2)[N:3]=1.C([Sn](CCCC)(CCCC)[C:18]1[N:22]2[CH:23]=[CH:24][C:25]([C:27]([F:30])([F:29])[F:28])=[N:26][C:21]2=[N:20][CH:19]=1)CCC>>[CH:8]1([C:4]2[N:3]=[C:2]([C:18]3[N:22]4[CH:23]=[CH:24][C:25]([C:27]([F:28])([F:29])[F:30])=[N:26][C:21]4=[N:20][CH:19]=3)[CH:7]=[CH:6][CH:5]=2)[CH2:12][CH2:11][CH2:10][CH2:9]1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 221807702-Bromo-6-cyclopentylpyridine

Product 1

HCID 99454713-(6-Cyclopentylpyridin-2-yl)-7-trifluoromethylimidazo[1,2-alpha]pyrimidineYield 10.5%

Procedure

2-Bromo-6-cyclopentylpyridine (479 mg, 2.1 mmol) was coupled to 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (1.4 mmol) by the method of Example 1 to give 3-(6-cyclopentylpyridin-2-yl)-7-trifluoromethylimidazo[1,2-α]pyrimidine (49 mg) as a white solid: δH (400 MHz, DMSO) 1.70-1.87 (6H, m), 2.10-2.16 (2H, m), 7.29 (1H, d, J 7.4), 7.80 (1H, d, J 7.0), 7.87 (1H, t, J 7.8), 7.95-7.97 (1H, m), 8.84 (1H, s), 10.50 (1H, d, J 6.7); m/z (ES+) 332 (M++H).

Sources & evidence

ORD record
ord-59be80a7733c40919a52943d75a7a384
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

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