Tert-butyl N-[5-methoxy-2-(2-oxopropyl)phenyl]carbamate → 6-methoxy-2-methyl-1H-indole

Participants

Reaction Steps

6-Methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-glyoxylic acid amide. Using the method in Example 9, Part C, 13.7 g 49 mmol) of 1-[2-(tert-butoxycarbonylamino)-4-methoxyphenyl]-2-propanone was reacted with 20 mL of trifluoroacetic and the produce chromatographed on silica eluting with 20% EtOAc/hexane. There was obtained 4.8 g (61% yield) of crude 6-methoxy-2-methyl-1H-indole. By the method in Example 6, Part A, this material (30 mmol) was treated with 1.2 g (30 mmol) of 60% NaH/mineral oil and 3.6 mL of benzyl bromide in DMF to give after chromatography on silica (eluting with 25% EtOAc/hexane) 4.77 g (63% yield) of 6-methoxy-2-methyl-1-(phenylmethyl)-1H-indole. By the method in Example 16, Part C, 1.97 g (8 mmol) of 6-methoxy-2-methyl-1-(phenylmethyl)-1H-indole was reacted with 0.73 mL (8.4 mmol) of oxalyl chloride and then ammonia to give 0.875 g (34% yield) of 6-methoxy-2-methyl-1-(phenylmethyl)-1H-indole-3-glyoxylic acid amide from EtOAc, mp, 230-234° C.

Provenance & Evidence