Triethylamine → 1-benzyl-1H-indole-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide

Participants

Reaction Steps

1-Benzyl-1H-indole-3-carbonyl chloride, prepared in the previous step, in 50 mL of anhydrous THF was added dropwise under nitrogen over 2 h to a mixture of 6-methylaminomethyl-naphthalen-2-ol (2.5 g, 13.37 mmol), prepared in step 1 of Example 32, and triethylamine (1.86 mL, 13.37 mmol) in 300 mL of anhydrous THF at room temperature. The reaction stirred for 17.5 h (overnight). A trace amount of solid was removed by filtration and the filtrate was concentrated under reduced pressure to give a brown oil. The oil was diluted with ethyl acetate, extracted two times with 1N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give 1-benzyl-1H-indole-3-carboxylic acid (6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (5.83 g, 100%) as a brown foam, MS m/z: 421 [M+H]+.

Provenance & Evidence