Cesium carbonate → HCID 67496634, compound

Participants

Reaction Steps

Phenol 64.D (248 mg, 0.56 mmol), methyl 2-bromoacetate (85 mg, 0.56 mmol), and Cs2CO3 (182 mg, 0.56 mmol) were mixed in DMF (1 ml) and stirred at room temperature for 1 h. The reaction mixture was partitioned with EtOAc/H2O and the aqueous layer was exctracted with EtOAc (3×). The organic layers were combined, dried with sodium sulfate, filtered, and concentrated. The crude product was first purified on a silica gel column (12 g, 0-10% MeOH:DCM) and then by prepHPLC(C18, ACN:H2O:0.1% TFA, gradient). The desired fractions were combined, partially concentrated on a rotavap, neutralized with NaHCO3 (sat), and extracted with DCM (2×). The organic layers were combined, dried with sodium sulfate, filtered, and concentrated to yield 64 (190 mg, 66%). LC-MS (+esi, M+H+=517.2). 1H NMR (400 MHz, MeOH) δ ppm 8.86 (d, J=1.96 Hz, 1H) 8.59 (d, J=2.35 Hz, 1H) 8.42 (d, J=5.09 Hz, 1H) 7.56 (s, 1H) 7.46-7.51 (m, 2H) 7.34 (d, J=1.96 Hz, 1H) 7.19-7.30 (m, 5H) 7.09 (d, J=8.61 Hz, 1H) 4.84 (s, 2H) 3.85-4.02 (m, 2H) 3.78 (s, 3H) 3.59 (dd, J=8.41, 4.89 Hz, 1H) 3.19 (dd, J=13.69, 5.09 Hz, 1H) 2.92 (dd, J=13.69, 8.61 Hz, 1H) 2.60 (s, 3H).

Provenance & Evidence