Sodium hydride → HCID 21867441, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the indole of Step 7 (800 mg, 2.4 mmol) in DMF (15 mL) was added NaH (136 mg, 3.4 mmol, 60% in oil) at 0° C. The reaction mixture was stirred at 0° C. for 15 minutes and tetra-n-butylammonium iodide (300 mg) was added, followed by the addition of ethyl 4-bromobutyrate (663 mg, 3.3 mmol). The resulting mixture was stirred for 2 h at r.t., quenched with saturated aqueous NH4Cl and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography eluted with 20% EtOAc in Hexanes to provide 690 mg of the title compound as a brown oil.

Provenance & Evidence