Ammonia → HCID 15469862, compound

Reaction equation

C(OC([O:11][C:12]1[N:13]([C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)=[O:23])[C:14]2[C:19]([CH:20]=1)=[CH:18][C:17]([Cl:21])=[CH:16][CH:15]=2)=O)C1C=CC=CC=1.N.O1CCOCC1>[Cl-].[Na+].O>[Cl:21][C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([C:22]([O:24][CH2:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)=[O:23])[C:12](=[O:11])[CH2:20]2

Participants

Procedure

Benzyl 2-{[(benzyloxy)carbonyl]oxy}-5-chloro-1H-indole-1-carboxylate, intermediate 37 (5.00 g; 11.47 mmol) was treated with a solution of ammonia in dioxane (25.2 ml; 0.50 M; 12.6 mmol) and stirred overnight. Brine was added and the mixture extracted with ethyl acetate. The organic phase was dried (MgSO4) and removed in vacuo, to give a solid residue which was purified by recrystallisation (ethyl acetate), to give the title compound in 59% yield (HPLC purity 88%). MS (ESI+): 302.1; MS (ESI−): 300.1