Boron Trichloride → HCID 78161917, compound

Participants

Reaction Conditions

Reaction Steps

To a 25-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 (355) (0.12 g, 0.27 mmol) and DCM (3 mL). The reaction mixture was cooled to −78° C. and under a N2 atmosphere boron trichloride (0.54 mL, 0.54 mmol, 1 M 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), eluted with a gradient of 2-7% 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 (360) (70 mg, 71% yield, 50% ee) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.80 (s, 1H), 8.05 (dd, J=1.17, 7.63 Hz, 1H), 7.68 (s, 1H), 7.63 (s, 1H), 7.61 (dd, J=1.17, 8.02 Hz, 1H), 7.37 (t, J=7.82 Hz, 1H), 7.03 (d, J=1.17 Hz, 1H), 5.20 (t, J=5.48 Hz, 1H), 4.54 (t, J=6.06 Hz, 1H), 3.66 (td, J=5.55, 10.61 Hz, 1H), 3.45-3.57 (m, 1H), 2.51 (s, 3H), 1.54 (s, 3H), 0.88-1.01 (m, 4H). m/z (ESI, +ve) 364.1 (M+H)+.

Provenance & Evidence