Sodium Methoxide → HCID 68508583, compound

Reaction equation

[NH2:1][CH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[C:10]1[N:11]([CH2:29][C:30](OC)=[O:31])[C:12]2[C:17]([C:18]=1[CH:19]1[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1)=[CH:16][CH:15]=[C:14]([C:25]([O:27][CH3:28])=[O:26])[CH:13]=2.C[O-].[Na+]>CO.CCOC(C)=O>[CH:19]1([C:18]2[C:17]3[CH:16]=[CH:15][C:14]([C:25]([O:27][CH3:28])=[O:26])=[CH:13][C:12]=3[N:11]3[CH2:29][C:30](=[O:31])[NH:1][CH2:2][C:3]4[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=4[C:10]=23)[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

Procedure

To a solution of methyl 2-[2-(aminomethyl)-4-fluorophenyl]-3-cyclohexyl-1-(2-methoxy-2-oxoethyl)-1H-indole-6-carboxylate (1 eq., from Step 3) in dry MeOH (0.05 M), 10% in weight of sodium methoxide was added and the mixture stirred at RT overnight. The volume of the solution was reduced in vacuo, before diluting with EtOAc. The organic phase was washed with HCl 1 N and brine, before being dried over Na2SO4, filtered and the solvent evaporated in vacuo to afford the title compound. The crude was used in the next step without further purification (83%); MS (ES+) m/z 421 (M+H)+.