Sodium Carbonate → HCID 89784085, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of Na2CO3 (102 mg, 0.959 mmol), Pd(Ph3)4 (18.47 mg, 0.016 mmol; Strem Chemicals), (2-chloropyridin-3-yl)boronic acid (75 mg, 0.480 mmol; Alfa Aesar, Ward Hil, Mass.), and 2-(3-chloro-2-methylquinoxalin-5-yl)-6,7-dihydro-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (100 mg, 0.320 mmol, 254c) was added to a conical vessel, sealed, and evacuated and backfilled with nitrogen three times. 1,4-dioxane (2.4 mL) and water (0.8 mL) were added via syringe, and the reaction was heated to 100° C. overnight. The reaction was cooled to RT and concentrated under reduced pressure to a residue. The residue was taken up in 2 mL DMSO, filtered through a syringe filter, and purified by reverse-phase preparative HPLC using a Xbridge C18 column (150 mm×30 mm, 10 mm), 40 mL min with 0.1% TFA in CH3CN/H2O, gradient 25% to 75% over 12 min. The product fractions were concentrated in a Genevac EZ-2 evaporator. The resulting solids were taken up in MeOH and eluted through a Si-carbonate cartridge (Silicycle, pre-washed with MeOH). The eluent was concentrated under reduced pressure to give 2-(3-(2-chloro-3-pyridinyl)-2-methyl-5-quinoxalinyl)-1,5,6,7-tetrahydro-4H-pyrrolo[3,2-c]pyridin-4-one (5 mg, 4%). 1H NMR (400 MHz, DMSO-d6) δ ppm 11.72 (1H, s) 8.84-8.98 (1H, m) 8.79 (1H, d, J=4.89 Hz) 8.08 (1H, dd, J=5.97, 2.64 Hz) 7.89-7.95 (2H, m) 7.82 (1H, d, J=4.89 Hz) 7.16-7.23 (1H, m) 7.01 (1H, br. s.) 3.33-3.43 (2H, m) 2.83 (2H, t, J=6.94 Hz) 2.54 (3H, s) m/z (ESI, +ve) 390.8 (M+H)+.

Provenance & Evidence