Sodium hydride → 3-[2'-(N-triphenylmethyltetrazol-5-yl)biphen-4-yl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine
Reaktionsgleichung
[CH2:1]([C:4]1[NH:5][C:6]2[C:7]([N:13]=1)=[N:8][CH:9]=[CH:10][C:11]=2[CH3:12])[CH2:2][CH3:3].[C:14]1([C:20]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:21]2[C:25]([C:26]3[C:31]([C:32]4[CH:37]=[CH:36][C:35]([CH2:38]Br)=[CH:34][CH:33]=4)=[CH:30][CH:29]=[CH:28][CH:27]=3)=[N:24][N:23]=[N:22]2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[H-].[Na+]>>[C:46]1([C:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=2)[N:21]2[C:25]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=3[C:32]3[CH:37]=[CH:36][C:35]([CH2:38][N:13]4[C:7]5=[N:8][CH:9]=[CH:10][C:11]([CH3:12])=[C:6]5[N:5]=[C:4]4[CH2:1][CH2:2][CH3:3])=[CH:34][CH:33]=3)=[N:24][N:23]=[N:22]2)[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1Komponenten
4
Versuchsvorschrift
3-[2'-(N-triphenylmethyltetrazol-5-yl)biphen-4-yl)methyl-7-methyl-2-propyl-3H-imidazo[4,5-b]pyridine was prepared according to the procedure described in Example 7, Part A from 2-propyl-7-methylimidazo[4,5-b]pyridine (991 mg, 5.66 mmol), N-triphenylmethyl-5-(4'-bromomethylbiphen-2-yl)tetrazole (3.0 g, 5.39 mmol), and NaH (6.47 mmol). Yield: 1.11 g (32%) thick oil; Rf: 0.80 (SiO2 tlc, 1:1 EtOAc-hexanes); 1H NMR (300 MHz, CDCl3) δ 8.20 (d, 1H, J=5 Hz), 7.89 (d, 1H, J=8 Hz), 7.51-7.39 (m, 2H), 7.38-7.20 (m, 10 H), 7.10-7.03 (m, 3H), 6.95-6.88, (m, 8H), 5.49 (s, 2H), 2.78-2.68 (m, 2H), 2.69 (s, 3H), 1.83-1.60 (m, 2H), 0.91 (t, 3H, J=5.5 Hz).
Quellen und Nachweise
- ORD-Eintrag
- ord-cc1065db005142b89f0d476fa73dae17
- Quelldatensatz
- uspto-grants-1994_07
- Patentnummer
- US05332744
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