Formaldehyde → HCID 71285431, compound

Participants

Reaction Steps

To a suspension of (R)-5-ethyl-6-(1-methyl-2-(pyrrolidin-2-yl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid hydrochloride (59.1 mg, 0.15 mmol) in dichloroethane (2.0 mL) was added aqueous NaHCO3 (0.20 mL). Reaction mixture was stirred at room temperature for 10 min before solution of HCHO (37% aqueous, 50 μL, 0.67 mmol) was added followed by AcOH (˜0.20 mL) to pH˜3-4. Upon addition of NaBH(OAc)3 (150 mg, 0.70 mmol) reaction was stirred at room temperature for 1 h. Complete consumption of starting material was observed. Mixture was quenched with addition of solution of NaHCO3 (aqueous saturated, 2 mL) and product was extracted with DCM (3×5 mL). Organic phase was dried over Na2SO4 and solvent was concentrated. Residue was triturated with Et2O and solid was collected by filtration to afford (R)-5-ethyl-6-(1-methyl-2-(1-methylpyrrolidin-2-yl)-1H-indol-5-yl)-2-oxo-1,2-dihydropyridine-3-carboxylic acid (40.0 mg, 72%) as yellow solid.

Provenance & Evidence