1-(1H-indol-6-yl)methanamine → 2-chloro-4-[[[(1H-indol-6-yl)methyl]amino]carbonyl]benzoic acid methyl ester
Reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:10][NH2:11])[CH:8]=2)[CH:3]=[CH:2]1.[CH3:12][O:13][C:14](=[O:32])[C:15]1[CH:20]=[CH:19][C:18]([C:21](ON2C(=O)CCC2=O)=[O:22])=[CH:17][C:16]=1[Cl:31]>CN(C)C=O>[CH3:12][O:13][C:14](=[O:32])[C:15]1[CH:20]=[CH:19][C:18]([C:21]([NH:11][CH2:10][C:7]2[CH:8]=[C:9]3[C:4]([CH:3]=[CH:2][NH:1]3)=[CH:5][CH:6]=2)=[O:22])=[CH:17][C:16]=1[Cl:31]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
1H-Indole-6-methanamine (Example 71; 0.9 g, 6.2 mmol) was added to a cooled (˜0° C.) solution of 2-chloro-4-[[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl]benzoic acid methyl ester (Example 73; 2.20 g, 7.1 mmol) in N,N-dimethylformamide and the solution was allowed to stir at room temperature overnight. The solvent was evaporated under high vacuum and ethyl acetate was added. The solution was washed in turn with 0.5N lo hydrochloric acid solution, saturated sodium bicarbonate solution and brine, then dried (MgSO4), filtered and evaporated in vacuo to afford 2-chloro-4-[[[(1H-indol-6-yl)methyl]amino]carbonyl]benzoic acid methyl ester (2.00 g, 94% yield).