Acetic Acid → 3-(2-tert-butylphenyl)-N-p-tolyl-1H-indole-1-carboxamide

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Reaction Steps

3-(2-tert-Butylphenyl)-1H-indole (24.1 mg, 0.0967 mmol) in 0.5 mL anhydrous tetrahydrofuran was treated with 1M NaN(TMS)2 in THF (0.2 mL) and stirred for 5 minutes at ambient temperature. 1-Isocyanato-4-methylbenzene (15 μL, 0.116 mmol) in 0.5 mL anhydrous tetrahydrofuran was added and stirred for 5 minutes at ambient temperature. 50 μL acetic acid and 200 μL methanol are added and the reaction mixture charged to a silica gel column and purified by eluting with a gradient of ethyl acetate and hexanes to give 3-(2-tert-butylphenyl)-N-p-tolyl-1H-indole-1-carboxamide which was further purified by reverse phase HPLC to give Example 49 (19.1 mg, 52%) as a colorless solid and 99.5% purity. LC/MS (ESI+) 383.4.

Provenance & Evidence