Sodium Carbonate → HCID 86593171, compound

Participants

Reaction Steps

Tert-butyl (±)-cis-2-bromo-5,6,8,9,11,11a-hexahydro-4H-pyrido[3′,4′:4,5]pyrrolo[3,2,1-ij]quinoline-10(7aH)-carboxylate (110 mg, 0.28 mmol) was dissolved in DME (4 mL). 2M aqueous sodium carbonate (0.75 ml) was added. 2,3-Dichlorophenylboronic acid (107 mg, 0.56 mmol) was added, followed by Pd2(dba)3 (14.5 mg, 0.014 mmol). P(Ph)3 (14.7 mg, 0.056 mmol) was added. The reaction flask was degassed and kept under a nitrogen atmosphere. The suspension was refluxed for 18 h cooled to rt. The reaction was concentrated in vacuo, after which water (10 mL) and EtOAc (10 mL) were added. The layers were separated and the aqueous phase was extracted with EtOAc (2×10 mL). The combined organic layers were washed with brine (2×10 mL), dried, and concentrated to afford a crude brown amorphous solid (162 mg). The residue was purified by column chromatography (20-0% hexane/CH2Cl2) to afford the title compound (96.8 mg, 75%) as a white amorphous solid. 1H NMR (CDCl3, 300 MHz) δ 7.61-7.94 (m, 1H), 7.20 (s, 1H), 7.18 (d, 1H, 3.3 Hz), 7.00 (s, 1H), 6.93 (s, 1H), 3.70-3.74 (m, 1H), 3.45-60 (m, 1H), 3.15-3.35 (m, 4H), 2.65-2.80 (m, 4H), 2.10-2.20 (m, 2H), 1.80-2.00 (m, 2H), 1.46 (s, 9H) ppm.

Provenance & Evidence