Cesium carbonate → HCID 24752878, compound

Participants

Reaction Conditions

Reaction Steps

Cesium carbonate (80 mg, 0.24 mmol) was added to a mixture of 1.1 (50 mg, 0.2 mmol), the benzyl chloride 1.4 (60 mg, 0.24 mmol) and CsI (catalytic amount) in DMSO (1 mL). The mixture was stirred at room temperature for 2 hours and at 35° C. for 4 hours. After cooling, the mixture was treated with EtOAc (5 mL) and brine (5 mL). The organic layer was separated, washed twice with brine, dried, and concentrated. The crude product was treated with THF (2 mL), MeOH (2 mL), water (1 mL) and NaOH (0.1 mL, 10 N). The mixture was stirred at room temperature for 4 hours. The organic solvent was blown away by nitrogen, and the aqueous mixture was acidified by adding HCl (0.35 mL, 3 N). The aqueous was extracted with DCM. The organic layer was dried, concentrated, and purified by flash chromatography to give 1 (40 mg). MS ESI (pos.) m/e: 448 (M+H). 1H NMR (CDCl3) δ 8.29 (d, 1H), 7.40 (m, 4H), 7.25 (m, 2H), 7.18 (m, 4H), 6.95 (d, 2H), 6.08 (d, 1H), 5.10 (s, 2H), 4.57 (t, 1H), 3.28 (dd, 1H), 2.99 (dd, 1H), 2.26 (s, 3H).

Provenance & Evidence