methyl 4-bromo-1H-indole-6-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of sodium hydroxide (14.08 g, 352.1 mmol) in water (100 mL) was added a to a solution of 4-bromo-1H-indole-6-carboxylic acid methyl ester in methanol (14.91 mL, 58.7 mmol) at room temperature and stirred for 2.5 hours. The reaction mixture was concentrated in vacuo, 1N HCl was added, and the product was extracted with ethyl acetate to give 13.0 g of 4-bromo-1H-indole-6-carboxylic acid, which was used in the next step with no further purification. 1H NMR (400 MHz, CD3OD) δ 8.13 (t, J=1.0 Hz, 1H), 7.87 (d, J=1.3 Hz, 1H), 7.53 (t, J=3.4 Hz, 1H), 8.13 (d, J=4.2 Hz, 1H). The reaction mixture was concentrated in vacuo, 1N HCl was added the product was extracted with ethyl acetate