Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylate → 2-Hydroxy-3-(5,6,7,8-tetrahydroquinazolin-4-yl)-1H-indole-5-carboxylic Acid Methyl Ester

반응식

CC(C)([O-])C.[Na+].[O:7]=[C:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]([O:19][CH3:20])=[O:18])[CH:14]=2)[NH:9]1.Cl[C:22]1[C:31]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=2[N:25]=[CH:24][N:23]=1>>[CH3:20][O:19][C:17]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([OH:7])=[C:16]2[C:22]1[C:31]2[CH2:30][CH2:29][CH2:28][CH2:27][C:26]=2[N:25]=[CH:24][N:23]=1)=[O:18]

참가 물질

반응물 3

HCID 2773516Methyl 2,3-dihydro-2-oxo-1H-indole-5-carboxylate

HCID 125829694-Chloro-5,6,7,8-tetrahydroquinazoline

HCID 23676156Sodium t-butoxide

생성물 1

HCID 1363519462-Hydroxy-3-(5,6,7,8-tetrahydroquinazolin-4-yl)-1H-indole-5-carboxylic Acid Methyl Ester

실험 절차

The title compound was synthesized according to the procedure described for Example 9 using sodium tert-butoxide (48 mg, 0.5 mmol), methyl 2-oxo-5-indolinecarboxylate (21 mg, 0.11 mmol) and 4-chloro-5,6,7,8-tetrahydroquinazoline solution (0.1 mL, 1 M in N-methylpyrrolidinone, corresponding to 17 mg, 0.1 mmol; described in: Budesinsky Z., Roubinek F. Collect. Czech. Chem. Commun., 1964, 29, 2341). The crude oil was purified on SCX-column pre-rinsed with methanol using ethyl acetate, methylene chloride, methylene chloride/methanol 1:1, and methanol/ammonia (2 M, aq) as elution solvents.