Sodium hydride → HCID 23594010, compound

Participants

Reaction Steps

A solution of 11-methoxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester, (0.155 g, 0.5 mM) in 5 mL DMF was added to a 60% NaH mineral oil dispersion (0.04 g, 1.0 mM, washed twice with hexane) at room temperature. Following cessation of gas evolution, benzyl bromide (0.067 mL, 0.094 g, 0.55 mM) was added and the mixture stirred at room temperature for 3 h. The mixture was diluted with ethyl acetate and H2O, the solvent layers separated, and the aqueous layer extracted with ethyl acetate (4×25 mL). The combined ethyl acetate extracts were washed with H2O, 1N HCl, saturated aqueous NaHCO3 solution, and saturated brine, dried over magnesium sulfate, filtered, concentrated in vacuo, and triturated with hexanes. The resultant tan solid was dried in vacuo, and purified by column chromatography on silica gel (elution with 9:1 toluene/ethyl acetate) to afford 0.133 g (66%) of the title compound 5-benzyl-11-methoxy-7,8,9,10-tetrahydro-5H-benzo[b]carbazole-1-carboxylic acid, methyl ester as an off-white foam (MP 144–146° C., MW 399.49).

Provenance & Evidence