Formaldehyde → HCID 89783587, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(3-(tert-butylamino)-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (193) (0.2 g, 0.57 mmol), K2CO3 (0.16 g, 1.14 mmol), and formaldehyde (Sigma-Aldrich) (0.46 mL of 37% wt. in water, 5.72 mmol) in THF (5.72 mL) were combined and stirred at 50° C. overnight. The reaction mixture was directly loaded onto a biotage and purified three times (0-100% EtOAc:EtOH (3:1)/hexane; 0-40% then 40% EtOAc:EtOH (3:1)/hexanes; then 0-20% then 20% EtOAc:EtOH (3:1)/hexanes) to yield the title compound (6 mg, 3% yield). 1H NMR (300 MHz, CDCl3) d ppm 1.49-1.75 (m, 23H) 2.56 (s, 3H) 2.95-3.10 (m, 2H) 3.20-3.34 (m, 1H) 3.74-3.91 (m, 2H) 4.79-4.92 (m, 1H) 4.98-5.08 (m, 2H) 7.01-7.14 (m, 1H) 7.31-7.46 (m, 1H) 7.59-7.72 (m, 1H) 7.89-8.03 (m, 1H) 12.51-12.65 (m, 1H). m/z (ES, +ve) 380.1 (M+H)+.

Provenance & Evidence