反应详情

A solution of 1.0 M boron tribromide in methylene chloride (55.0 mL, 54.9 mmol) in 50 mL of methylene chloride was added under nitrogen dropwise over 1.5 h to a solution of 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-methoxy-naphthalen-2-ylmethyl)-methyl-amide (8.0 g, 18.3 mmol), prepared in the previous step, in 300 mL of methylene chloride at dry ice-acetone temperature. The dry ice-acetone bath was replaced with an ice bath immediately after the addition. The reaction stirred at ice bath temperature for 2 h. At ice bath temperature, the reaction was quenched by the dropwise with water. The reaction was partitioned between methylene chloride and water. A solid formed in the organic layer and was collected by filtration. The solid was dried under reduced pressure to give 1-methyl-1H-indole-3-carboxylic acid (5-bromo-6-hydroxy-naphthalen-2-ylmethyl)-methyl-amide (6.5359 g, 84%) as a white solid, mp 189-190° C.

1. additionimmediately after the addition
2. customAt ice bath temperature, the reaction was quenched by the dropwise with water
3. customThe reaction was partitioned between methylene chloride and water
4. customA solid formed in the organic layer
5. filtrationwas collected by filtration
6. customThe solid was dried under reduced pressure