Hydrochloric Acid → {5-[N-(cyclopentylmethyl)-N-ethylamino]-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl}methanol

Participants

Reaction Conditions

Reaction Steps

A solution of 5-[N-(cyclopentylmethyl)-N-ethylamino]-methyl-1H-pyrrolo[3,2-b]pyridine-6-carbonitrile (0.30 g, 1.06 mmol) in methoxyethanol (6 mL) is treated with 5N NaOH aq. (6 mL). The reaction mixture is stirred at 130° C. for 60 hours. After cooling to room temperature, the mixture is acidified with 1N HCl. The mixture is extracted with CH2Cl2, dried over sodium sulfate and concentrated in vacuo. To a solution of the obtained residue in THF (5 mL) is added triethylamine (0.14 mL, 1.00 mmol) and ethyl chloroformate (0.10 mL, 1.00 mmol) at room temperature. After stirring for 1 h, the resulting precipitate is removed by filtration, and the filtrate is concentrated in vacuo. To a solution of the residue in EtOH (3 mL) is added sodium borohydride (41 mg, 1.08 mmol) at 0° C. After stirring for 1 h, the reaction is quenched with H2O. The mixture is extracted with EtOAc and washed with brine. The organic layer is dried over sodium sulfate and concentrated in vacuo. The residue is purified by silica-gel column chromatography to give {5-[N-(cyclopentylmethyl)-N-ethylamino]-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl}methanol as a colorless oil.

Provenance & Evidence