Boron Trichloride → HCID 78161917, compound

Participants

Reaction Conditions

Reaction Steps

To a 50-mL round-bottomed flask was added 6-((benzyloxy)methyl)-2-(2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (364) (0.27 g, 0.63 mmol) and DCM (10 mL). The reaction mixture was cooled to −78° C. and under a N2 atmosphere boron trichloride (1.25 mL, 1.25 mmol, 1M in DCM) (Sigma-Aldrich Chemical Company, Inc.) was added dropwise. The reaction mixture was stirred at −78° C. for 30 min and at 0° C. for 30 min. The reaction was quenched by the addition of NaHCO3 (100 mg in MeOH, 3 mL) and the solvent was removed under vacuum. The crude material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (12 g), eluting with a gradient of 2-8% MeOH in DCM to provide 6-(hydroxymethyl)-2-(2-methyl-3-((1-methylcyclopropyl)amino)quinoxalin-5-yl)-5,6-dihydropyrrolo[3,4-b]pyrrol-4(1H)-one (365) (50% ee) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 13.17 (s, 1H), 8.04 (dd, J=1.17, 7.63 Hz, 1H), 7.58-7.63 (m, 2H), 7.55 (s, 1H), 7.36 (t, J=7.82 Hz, 1H), 6.97 (d, J=1.17 Hz, 1H), 5.21 (t, J=5.28 Hz, 1H), 4.48 (dd, J=6.06, 8.02 Hz, 1H), 3.74 (td, J=5.21, 10.12 Hz, 1H), 3.20-3.28 (m, 1H), 2.92 (dt, J=2.93, 6.46 Hz, 1H), 2.51 (s, 3H), 1.00-1.13 (m, 1H), 0.86-0.96 (m, 1H), 0.75-0.85 (m, 1H), 0.44-0.55 (m, 1H). m/z (ESI, +ve) 350.3 (M+H)+.

Provenance & Evidence