Ethanol → [4-(1-cyclopropylmethyl-6-ethoxy-3-iodo-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-Cyclopropylmethyl-6-ethoxy-3-iodo-2-(4-nitro-phenyl)-1H-indole (990 mg, 2.14 mmol), iron powder (690 mg, 11.8 mmol), NH4Cl (690 mg, 12.9 mmol), ethanol (22 mL), and H2O (8 mL) were heated at 80° C. for 90 minutes. The reaction mixture was diluted with H2O and extracted with CH2Cl2. The organic layer was dried, concentrated and purified by silica gel chromatography (CH2Cl2). Product containing fractions were used immediately in the next reaction. The compound in CH2Cl2 (80 mL) was treated with pyridine (15 mL) and isopropylchloroformate (1M in toluene, 2.5 mL, 2.5 mmol) and stirred at room temperature for 15 minutes. The reaction mixture was concentrated and extracted with a mixture of EtOAc and aq. HCl. The organic layer was washed with H2O and brine and then dried, concentrated and purified by silica gel chromatography (CH2Cl2/hexane, 1:1 to 3:1) to provide [4-(1-cyclopropylmethyl-6-ethoxy-3-iodo-1H-indol-2-yl)-phenyl]-carbamic acid isopropyl ester (644 mg, 58%) as a white solid.

Provenance & Evidence