Sodium hydride → Methyl 1-[4-(trifluoromethyl)benzyl]-1H-indole-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 1H-indole-7-carboxylate (47.8 g, 273 mmol) and 1-(bromomethyl)-4-(trifluoromethyl)benzene (81 g, 341 mmol) were dissolved in DMF (1.3 L) at 0° C. 60% w/w NaH (12 g, 300 mmol) was added portion wise. The ice bath was removed and the mixture stirred at 0° C. for 3 hours, then overnight at RT. The reaction mixture was quenched with 3 L of NH4Cl(sat.) and the aqueous layer was extracted 3 times with 1 L of ether. The organic layers were combined, washed with water and brine. The compound was purified by flash chromatography on silica gel. 1H NMR (500 MHz, DMSO-d6): δ 8.90 (d, 1H), 7.70 (s, 1H), 7.60 (d, 2H), 7.40 (d, 1H), 7.10 (t, 1H), 7.00 (d, 2H), 6.70 (d, 1H), 5.70 (s, 2H).

Provenance & Evidence