Hydrochloric Acid → HCID 68506576, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of methyl 3-cyclohexyl-1-(2,2-dimethoxyethyl)-2-[2-({[2-(dimethylamino)ethyl]amino}methyl)phenyl]-1H-indole-6-carboxylate (0.16 M, 1 eq, from Step 3) in THF was added an equal volume of aqueous 1N HCl. The reaction was heated at 60° C. for 2.5 h and after cooling to RT was quenched by addition of NaOH (2N) and extracted into EtOAc (×3). The combined organic extracts were washed with brine before being dried over Na2SO4, filtered and concentrated in vacuo. The residue was re-dissolved in MeOH and acidified to pH 4 with glacial acetic acid. After stirring for 45 min, NaBH4 (8 eq) was added portionwise until cyclisation was complete as evidenced by LC-MS analysis. The reaction was quenched by addition of sat. aq. NaHCO3 and extracted into EtOAc (×3). The combined organic extracts were washed with brine before being dried (Na2SO4), filtered and concentrated in vacuo. The title compound was obtained as a pale yellow oil and taken on without further purification (quant.); MS (ES+) m/z 460 (M+H)+.

Provenance & Evidence