4-Methoxybenzenesulfonyl chloride → HCID 51355175, compound

Participants

Reaction Conditions

Reaction Steps

A round bottom flask was charged with 5-bromo-2-chloropyridin-3-amine (2.50 g, 12.1 mmol) and 24 mL THF and the solution was cooled to −78° C. under nitrogen. 1.0 M LiHMDS (24.1 ml, 24.1 mmol) was added slowly and the solution was stirred for 10 min at −78° C. 4-methoxybenzene-1-sulfonyl chloride (3.49 g, 16.9 mmol) dissolved in a minimum amount of THF (˜5 mL) was added slowly, and the cooling bath was removed after 10 min. The reaction was stirred at room temperature overnight and was quenched with saturated NH4Cl. The layers were separated, and the organic portion was diluted with CH2Cl2, washed with 1 N HCl and brine. The organic portion was dried with MgSO4, filtered and concentrated. The crude material was dissolved in CH2Cl2 (˜20 mL) and ether was added (˜40 mL) in portions over 15 min. After allowing to stand in the freezer for 1 h, the solids were filtered and washed with ether. N-(5-bromo-2-chloropyridin-3-yl)-4-methoxybenzenesulfonamide (3.127 g, 68.7% yield) was isolated as a white crystalline solid. MS (ESI pos. ion) m/z calc'd for C12H10BrClN2O3S: 377.6. found 378.8.

Provenance & Evidence