Water → Indole

Participants

Reaction Conditions

Reaction Steps

[Pd(dppf)Cl2×CH2Cl2]; 327 mg, 0.4 mmol) was then added. The reaction mixture was stirred at 100° C. (oil bath temperature) for 6 h and at room temperature for 18 h. The reaction mixture was then cooled with ice water, water (50 ml) and ethyl acetate (100 ml) were added and the mixture was stirred for 30 min. In order to separate off the catalyst, the dark brown mixture was filtered over Celite. The phases of the filtrate were separated. The aqueous phase was extracted with ethyl acetate (5×35 ml). The combined organic phases were washed with saturated sodium chloride solution (3×35 ml), subsequently dried with sodium sulfate, filtered and concentrated in vacuo. The dark brown oil obtained (1.8 g) which, apart from 3-methyl-5-trifluoromethyl-2-trimethylsilanyl-1H-indole, contained traces of DMF and also the isomer 2-methyl-5-trifluoromethyl-3-trimethylsilanyl-1H-indole, was employed as the crude product for the next stage.

Provenance & Evidence