Methylamine → 5-Aminoindole

Participants

Reaction Steps

Compound 245 was prepared using methods shown in Example 1, wherein 2-fluoro-5-nitrobenzonitrile and methylamine were used in Step A and methyl anthranilate was used in Step D. Reduction of the 5-nitro group was carried out using stannous chloride in ethanol to provide the corresponding 5-amino indole intermediate. Dimethylation of the 5-amino group was carried out using aqueous formaldehyde solution (37% w/w, 10 eq.) and MP-cyanoborohydride resion (2.42 mmol/g, 1.5 eq.) in methanol:acetic acid (9:1, v/v) at room temperature for about 15 hours.

Provenance & Evidence