Chloride → HCID 178441200, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-butyl-1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-cyanomethoxy-naphthalen-2-ylmethyl)-methyl-amide (1.79 g, 3.45 mmol), prepared in the previous step, sodium azide (673 mg, 10.35 mmol) and ammoniun chloride (554 mg, 10.36 mmol) in 100 mL of DMF was stirred under nitrogen at 100° C. for 4.25 h. The reaction was diluted with water, made basic by the addition of 20 mL of 1 N NaOH and extracted multiple times with ethyl acetate. The aqueous layer was acidified with 40 mL of 1 N HCl. A brown oil separated. The oil was partitioned between the aqueous layer and methylene chloride. The organic layer separated and the aqueous layer was extracted three times with methylene chloride. The combined extracts were dried (MgSO4) and the solvent removed under reduced pressure. The residue was dissolved in 20 mL of 1 N NaOH and then acidified with 30 mL 1 N HCl. The solid that formed was collected by filtration, rinsed with water and dried under reduced pressure to give the title compound (1.75 g, 89%) as an off-white solid, mp 147-149° C.

Provenance & Evidence