2-Ethoxy-1-naphthoic acid → Ethyl [2-(2-ethoxy-naphthalene-1-carbonyl)-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl]-acetate

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Reaction Steps

Step a): To a solution of 2-ethoxynaphthoic acid (22 mg, 0.1 mmol), N′,N′,N′,N′tetramethyl-O-(7-azabenzotriazole-1-yl)-uronium-hexafluorophosphate (38 mg, 0.1 mmol) and DIEA (51 μl, 0.3 mmol) in THF/DMF (4:1, 1 ml) is added Intermediate 1 (29 mg, 0.1 mmol) in one portion and the reaction mixture is stirred at rt overnight. Then, the solvent is evaporated and the residue purified by silica gel column chromatography (6% MeOH in CH2Cl2/aqueous NH4OH 9:1) affording ethyl [2-(2-ethoxy-naphthalene-1-carbonyl)-1,2,3,4-tetrahydro-pyrido[4,3-b]indol-5-yl]-acetate (43 mg) as a glassy brown solid in 93% yield.

Provenance & Evidence