tert-Butyl 4'-(bromomethyl)biphenyl-2-carboxylate → 3-(2'-carboxybiphen-4-yl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridin
Reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]=[C:9]([CH2:11][CH2:12][CH3:13])[NH:10][C:3]=12.C([O:18][C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][C:30]([CH2:33]Br)=[CH:29][CH:28]=1)=[O:20])(C)(C)C>>[C:19]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[C:27]1[CH:32]=[CH:31][C:30]([CH2:33][N:8]2[C:4]3=[N:5][CH:6]=[CH:7][C:2]([CH3:1])=[C:3]3[N:10]=[C:9]2[CH2:11][CH2:12][CH3:13])=[CH:29][CH:28]=1)([OH:20])=[O:18]Participants
3
Procedure
7-Methyl-2-propylimidazo[4,5-b]pyridine (described in Example 9) was alkylated with 2-t-butoxycarbonyl-4'-bromomethylbiphenyl and the resulting protected derivative was deprotected according to the procedure described in Step 2 of Example 3. NMR (CDCl3): δ 0.93 (t, J=7.5 Hz, 3H), 1.69 (q, 2H), 2.63 (s, 3H), 2.78 (t, J=7.5 Hz, 2H), 5.49 (s, 3H), 7.04-7.5(m, 8H), 7.8 (d, J=2.4 Hz, 1H), 8.14 (d, J=5 Hz, 1H). FAB-MS: m/e 386 (M+H).
Sources & evidence
- ORD record
- ord-712f61e012db4ef3aa290b853bda94ad
- Source dataset
- uspto-grants-1994_07
- Patent number
- US05332744
Reaction notes
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