8-Quinolinesulfonyl chloride → HCID 68233375, compound

Participants

Reaction Steps

To a mixture of compound 14f (crude, 129 mg, 0.5 mmol) in pyridine (4 mL) at rt was added quinoline-8-sulfonyl chloride (142 mg, 0.6 mmol). The reaction mixture was stirred for 16 h and concentrated under reduced pressure. The residue was partitioned between CHCl3 and H2O. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by Prep-TLC to give compound 14 (100 mg, 44% yield). 1H NMR (400 MHz, CDCl3) δ 8.97 (s, 1H), 8.49 (d, 1H, J=8.0 Hz), 8.17 (d, 1H, J=8.0 Hz), 7.97 (d, 1H, J=8.0 Hz), 7.56 (t, 1H, J=8.0 Hz), 7.47-7.44 (m, 1H), 7.21 (d, 1H, J=8.0 Hz), 7.02-7.00 (m, 1H), 6.94-6.93 (m, 1H), 6.87 (d, 1H, J=8.0 Hz), 5.17 (d, 1H, J=8.0 Hz), 4.98-4.93 (m, 2H), 4.66 (d, 1H, J=8.0 Hz), 4.51 (s, 1H), 4.27 (d, 1H, J=8.0 Hz), 3.78 (d, 1H, J=8.0 Hz), 3.53 (t, 1H, J=7.2 Hz), 3.21-3.18 (m, 1H), 1.00 (s, 9H). MS (ESI) calcd for [C24H28N2O4S+H]+ (m/z): 441.56. found: 441.3.

Provenance & Evidence