4-Iodo-2-methoxy-3-(5-phenyl-1H-imidazol-2-yl)-pyridine → 4-Ethyl-2-(4-iodo-2-methoxy-pyridin-3-yl)-5-phenyl-imidazol-1-ol
Reaction equation
I[C:2]1C=CN=C(OC)[C:3]=1C1NC(C2C=CC=CC=2)=CN=1.[I:21][C:22]1[CH:27]=[CH:26][N:25]=[C:24]([O:28][CH3:29])[C:23]=1[C:30]1[N:31]([OH:41])[C:32]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)=[CH:33][N:34]=1>>[CH2:2]([C:33]1[N:34]=[C:30]([C:23]2[C:24]([O:28][CH3:29])=[N:25][CH:26]=[CH:27][C:22]=2[I:21])[N:31]([OH:41])[C:32]=1[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)[CH3:3]Participants
Procedure
4-Iodo-2-methoxy-3-(5-phenyl-1H-imidazol-2-yl)-pyridine and 2-(4-iodo-2-methoxy-pyridin-3-yl)-5-phenyl-imidazol-1-ol: Isonitrosoacetophenone (0.030 g, 0.114 mmol) was reacted as described for the synthesis of 4-ethyl-2-(4-iodo-2-methoxy-pyridin-3-yl)-5-phenyl-imidazol-1-ol and gave 4-iodo-2-methoxy-3-(5-phenyl-1H-imidazol-2-yl)-pyridine (0.008 g, 19%) and 2-(4-iodo-2-methoxy-pyridin-3-yl)-5-phenyl-imidazol-1-ol (0.007 g, 16%). 4-Iodo-2-methoxy-3-(5-phenyl-1H-imidazol-2-yl)-pyridine: LCMS (+ESI, M+H+) m/z 378; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 3.83 (3H, s), 7.17-7.97 (8H, m), 12.29 and 12.60 (1H, 2 br s). 2-(4-Iodo-2-methoxy-pyridin-3-yl)-5-phenyl-imidazol-1-ol: : LCMS (+ESI, M+H+) m/z 378; 1H NMR (400 MHz, DMSO-d6) δ (ppm): 3.82 and 3.92 (3H, 2 d), 7.19-8.05 (8H, m), 11.68 and 12.70 (1H, 2s).
Sources & evidence
- ORD record
- ord-24553b9332a2497a841db16cef4aa571
- Source dataset
- uspto-grants-2008_12
- Patent number
- US07470713B2
Reaction notes
Loading…