Sodium hydride → N-[6-Cyano-9-(2-methoxy-benzyl)-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide

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Reaction Steps

Follow the procedures essentially as described in Example 104, above, using N-(6-cyano-2,3,4,9-tetrahydro-1H-carbazol-3-yl]-isobutyramide (3.38 g, 12 mmol) and treating with sodium hydride (580 mg, 14A mmol). Cool the formed sodium salt in a dry ice/acetonitrile bath and add 2-methoxybenzylchloride (1.84 mL, 13.2 mmol) in DMF (2 mL) at −35 to −30° C. Remove the bath and allow the reaction to warm to ambient temperature over 3 h with stifling. Add water (250 mL) dropwise, cooling in an ice bath while stirring for 30 min. Filter the resulting precipitate and dry under house vacuum at 45° C. for 18 h. Triturate and sonicate the material in diethyl ether for 1.5 h, filter and dry to provide 3.98 g (83%) of an off-white solid.

Provenance & Evidence