Sulfuryl chloride → HCID 11249869, compound

Participants

Reaction Steps

To a solution of 3-(4-Amino-phenylsulfanyl)-4-(5-chloro-2-methoxy-phenyl)-6-trifluoromethyl-1H-quinolin-2-one or 3-(4-Amino-phenylsulfanyl)-4-(5-chloro-2-hydroxy-phenyl)-6-trifluoromethyl-1H-quinolin-2-one (49.0 mg, 103 μmol, 1 eq) in pyridine (50 μL) and methylene chloride (500 μL) was added the appropriate sulfonyl chloride (422 μmol, 4.1 eq), and the mixture stirred overnight at room temperature, or at 80° C. in the absense of methylene chloride for difficult cases. The pyridine was removed in vacuo, and 4 N NaOH was added. The suspension was diluted with water, washed with chloroform, and adjusted to pH 5 with 1 M HCl. The product was extracted into a mixture of EtOAc and methylene chloride, dried with Magnesium sulfate, and concentrated in vacuo. Final purification was effected by reverse phase HPLC to afford pure Ib. 1H NMR (300 MHz, CDCl3) δ 11.04 (s, 1H), 8.90 (s, 1H), 7.67 (d, J=8.6 Hz, 1H), 7.43 (s, 1H), 7.40–7.30 (m, 2H), 7.30–7.24 (m, 3H), 7.11 (d, J=2.5 Hz, 1H), 6.98 (d, J=8.7 Hz, 1H), 6.91 (d, J=8.7 Hz, 2H), 2.99 (q, J=7.4 Hz, 2H), 1.21 (t, J=7.4 Hz, 3H); LCMS (M+H) 555, RT=3.177 (Method 1).

Provenance & Evidence