2,6-Dichlorobenzenesulfonylchloride → HCID 44609705, compound

Participants

Reaction Conditions

Reaction Steps

(Some starting materials may be obtained from Alfa Aesar, Ward Hills, Mass.) To a flame-dry 50 mL rb flask was added 2-chloro-5-(4-morpholinoquinolin-6-yl)pyridin-3-amine (0.07 g, 0.2 mmol) and THF (8 mL). The reaction mixture was cooled to 0° C. followed by adding sodium bis(trimethylsilyl)amide, 1.0 m solution in tetrahydrofuran (0.4 mL, 0.4 mmol). After the addition, it was continued to stir at 0° C. under N2. After 30 min, 2,6-dichlorobenzene-1-sulfonyl chloride (0.07 g, 0.3 mmol) was added into the reaction mixture. After the addition, it was continued to stir at 0° C. then slowly warmed up to rt overnight. The reaction was quenched with water. The solvent was concentrated. The residue was partitioned between EtOAc/water. The organic layer was washed with brine, dried over MgSO4 and concentrated. The crude product was purified using SiO2 (12 g) chromatography with DCM:EtOAc:MeOH=70%:26%:4% as the solvent system to afford the desired product as light yellow solid (63.0 mg). MS (ESI pos. ion) m/z: calc'd for C24H19Cl3N4O3S: 548.1; found: 549.4 (M+1). 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 3.21-3.38 (m, 4 H) 3.93-4.11 (m, 4 H) 6.94 (d, J=4.97 Hz, 1 H) 7.33-7.44 (m, 1 H) 7.45-7.55 (m, 2 H) 7.85 (dd, J=8.77, 2.05 Hz, 1 H) 8.18 (d, J=8.77 Hz, 1 H) 8.25 (d, J=1.90 Hz, 1 H) 8.39-8.50 (m, 2 H) 8.81 (d, J=4.97 Hz, 1 H).

Provenance & Evidence