反应详情

1-((1,1′-Biphenyl)-3-ylmethyl)-4-hydroxy-2-methyl-1H-indole (1030 mg, 3.3 mmol) is alkylated by treating with 0.31 mL (3.3 mmol) of methyl bromoacetate and 132 mg (3.3 mmol) and 132 mg (3.3 mmol) of 60% NaH/mineral oil in DMF and stirring maintained for about 17 hours. The mixture is diluted with water and extracted with ethyl acetate. The ethyl acetate solution is washed with brine, dried (MgSO4), and concentrated at reduced pressure. The product is purified by chromatography over silica gel eluting with 20% EtOAc/hexane, to give 1000 mg (79% yield) of ((1-((1,1′-biphenyl)-3-ylmethyl)-2-methyl-1H-indol-4-yl)oxy)acetic acid methyl ester; mp 99°-102° C.

1. temperaturemaintained for about 17 hours
2. extractionextracted with ethyl acetate
3. washThe ethyl acetate solution is washed with brine
4. dry with materialdried (MgSO4)
5. concentrationconcentrated at reduced pressure
6. customThe product is purified by chromatography over silica gel eluting with 20% EtOAc/hexane