Water → 5-(Cyclopentylmethyl)-6-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one

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Reaction Steps

A stirred solution of 6-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (1.023 g) in dry DMF (50 ml) was treated with sodium hydride (73.2% dispersion in oil; 331 mg) and stirred under nitrogen at room temperature for 30 min. A solution of cyclopentylmethyl(methyl sulphonate (893 mg) in dry DMF (20 ml) was then added over 15 min and stirring was continued for 5 days. Water (20 ml) was added to the reaction mixture which was then concentrated in vacuo to give a solid. This was dissolved in ethyl acetate (300 ml) and methanol (1 ml), and the resulting solution was washed with saturated sodium chloride solution (3×100 ml) and then adsorbed onto silica. Purification by FCC eluting with System A (150:8:1) gave a solid (283 mg) which was recrystallised from ethyl acetate to give the title compound (237 mg) m.p. 175°-176°.

Provenance & Evidence