Toluene → 3-Methyl-4-(5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-5-yl)benzonitrile
Reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]1[N:15]2[CH:16]=[N:17][CH:18]=[C:14]2[CH2:13][CH2:12][CH2:11]1)[C:5]#[N:6].[C:19]1(C)C=CC=CC=1>>[CH3:19][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH:10]1[N:15]2[CH:16]=[N:17][CH:18]=[C:14]2[CH2:13][CH2:12][CH2:11]1)[C:5]#[N:6]Participants
3
Procedure
3-Bromo-4-(5,6,7,8-tetrahydro-imidazo[1,5-a]pyridin-5-yl)benzonitrile, prepared above, is converted to the corresponding toluene by the method outlined in Tet. Lett. 2000, 41, 6237. MS (ESI) m/z 238.1 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.77-1.89 (m, 2H), 1.91-2.00 (m, 1H), 2.29-2.39 (m, 1H), 2.45 (s, 3H), 2.86-2.93 (m, 2H), 5.71 (t, J=6.1 Hz, 1H), 6.77 (d, J=8.1 Hz, 1H), 6.81 (s, 1H), 7.29 (s, 1H), 7.49 (d, J=8.1 Hz, 1H), 7.61 (s, 1H).
Sources & evidence
- ORD record
- ord-1b539d3c843d486690970b76c5899484
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08835646B2
Reaction notes
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