Pyridine → HCID 59128704, compound

Participants

Reaction Steps

PhSO2Cl (24 mg, 0.136 mmol) was added dropwise over a period of 3 min. to a stirred solution of 42 (31 mg, 0.090 mmol) and pyridine (11.4 mg, 0.144 mmol) in CH2Cl2. The mixture was stirred at r.t. overnight. Additional portion of PhSO2Cl (24 mg, 0.136 mmol) was added, followed by DMAP (3 mg, 0.025 mmol). After additional stirring for 1.5 h, the mixture was partitioned between saturated aqueous NaHCO3:CH2Cl2. The aqueous layer was extracted with CH2Cl2. The combined organic solutions were washed with brine, dried (MgSO4) and concentrated. Purification by PTLC using AcOEt:hexane=1:1 (v/v) as eluent afforded 43 as orange powder (15 mg, 35%). 1H NMR (400 MHz; CDCl3) δ 7.55 (tt, J=6.6, 1.6 Hz, 2H), 7.62 (tt, J=5.3, 2.0 Hz, 1H), 7.84 (dd, J=5.4, 3.0 Hz, 2H), 7.88 (s, 1H), 7.92 (d, J=2.3 Hz, 1H), 7.98 (dd, J=5.4, 3.0 Hz, 2H), 8.23 (dd, J=4.0, 1.3 Hz, 2H), 8.55 (d, J=1.9 Hz, 1H).

Provenance & Evidence