Imidazo[1,2-a]pyrimidine, 3-(tributylstannyl)-7-(trifluoromethyl)- → 4-Fluoro-2-[6-(7-trifluoromethylimidazo[1,2-alpha]pyrimidin-3-yl)pyridin-2-yl]benzonitrile
Reaction equation
C([Sn](CCCC)(CCCC)[C:6]1[N:10]2[CH:11]=[CH:12][C:13]([C:15]([F:18])([F:17])[F:16])=[N:14][C:9]2=[N:8][CH:7]=1)CCC.Br[C:28]1[N:33]=[C:32]([C:34]2[CH:41]=[C:40]([F:42])[CH:39]=[CH:38][C:35]=2[C:36]#[N:37])[CH:31]=[CH:30][CH:29]=1>>[F:42][C:40]1[CH:39]=[CH:38][C:35]([C:36]#[N:37])=[C:34]([C:32]2[CH:31]=[CH:30][CH:29]=[C:28]([C:6]3[N:10]4[CH:11]=[CH:12][C:13]([C:15]([F:16])([F:17])[F:18])=[N:14][C:9]4=[N:8][CH:7]=3)[N:33]=2)[CH:41]=1Participants
3
Procedure
3-Tributylstannyl-7-trifluoromethylimidazo[1,2-α]pyrimidine was coupled with 2-(6-bromopyridin-2-yl)-4-fluorobenzonitrile as in Example 1 to give 4-fluoro-2-[6-(7-trifluoromethylimidazo[1,2-α]pyrimidin-3-yl)pyridin-2-yl]benzonitrile as a pale pink solid (16 mg, 14%): δH (400 MHz, CDCl3) 7.29-7.32 (1H, m), 7.40 (1H, d, J 7), 7.53 (1H, dd, J 9 and 2), 7.66 (1H, dd, J 8 and 1), 7.88-8.03 (3H, m), 8.59 (1H, s), 10.56 (1H, d, J 7).
Sources & evidence
- ORD record
- ord-e4f03d2588b74b328d0db7ece854cbd9
- Source dataset
- uspto-grants-2006_04
- Patent number
- US07030128B2
Reaction notes
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