Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → HCID 9947245, compound

HRID 1796010Notes

Reaction equation

HRID 1796010 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]2[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=2[C:10]#[N:11])[CH:3]=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:32][C:30]([F:31])([F:33])[C:28]1[CH:27]=[CH:26][N:25]2[C:21]([C:2]3[CH:7]=[CH:6][N:5]=[C:4]([C:8]4[CH:15]=[CH:14][CH:13]=[CH:12][C:9]=4[C:10]#[N:11])[CH:3]=3)=[CH:22][N:23]=[C:24]2[N:29]=1

Participants

3

Reactant 2

HCID 11294484Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)-HCID 22180771HCID 22180771, compound

Product 1

HCID 9947245HCID 9947245, compoundYield 13.7%

Procedure

2-(4-Chloropyridin-2-yl)benzonitrile (65 mg, 0.3 mmol) was coupled with 3-tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine (0.6 mmol) as described in Example 1 to give 2-[4-(7-trifluoromethyl-imidazo[1,2-α]pyrimidin-3-yl)pyridin-2-yl]benzonitrile (15 mg) as a white solid: δH (400 MHz, DMSO) 7.62 (1H, d, J 7.0), 7.69 (1H, m), 7.88 (1H, m), 7.93 (1H, dd, J 5 and 2), 8.04 (2H, m), 8.27 (1H, d, J 1), 8.60 (1H, s), 8.92 (1H, dd, J 5 and 1), 9.60 (1H, d, J 8); m/z (ES+) 366 (M++H).

Sources & evidence

ORD record
ord-febf6bd5b7964f5e96c2b15ac4ffe843
Source dataset
uspto-grants-2006_04
Patent number
US07030128B2

Reaction notes

Loading…