Trifluoroacetic acid → HCID 71284361, compound

Participants

Reaction Steps

To a solution of methyl 1-(2,4-dimethoxybenzyl)-5-ethyl-2-oxo-6-(1-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indol-7-yl)-1,2-dihydropyridine-3-carboxylate (0.11 g, 0.22 mmol) in DCE (2 mL) was added pyrrolidine (80 μL, 0.88 mmol) and AcOH (30 μL). After stirring at room temperature for 1 h, NaBH(OAc)3 (0.1 g, 0.44 mmol) was added and the reaction mixture was stirred for an additional 2 h before TFA (1.5 mL) was added. After stirring for 30 min, the reaction mixture was concentrated and the crude residue was dissolved in THF (1 mL) and aqueous NaOH (2 mL, 4M) was added and the resulting mixture was heated to 60° C. for 15 h. The reaction mixture was then poured into H2O, acidified with 4M HCl, and extracted with CH2Cl2 (2×30 mL). The combined organic phases were dried over Na2SO4, filtered, and concentrated in vacuo to afford a crude oil which was triturated with Et2O to afford the title compound as an orange solid (35 mg, 41% over 3 steps).

Provenance & Evidence