反应详情

5-Bromo-2-chloropyridin-3-amine (1.535 g, 7.399 mmol, Asymchem Laboratories, Morrisville, N.C.) was dissolved in pyridine (20 mL), and 4-acetylbenzenesulfonyl chloride (2.436 g, 11.14 mmol) was added. The reaction flask was fit with a reflux condensor and placed in a preheated oil bath (110 C-115 C) and stirred under nitrogen for 2 hours. The reaction was then cooled to room temperature, concentrated, and poured into a biphasic solution of water (40 mL) and DCM (50 mL). The layers were separated, and the aqueous phase was extracted with DCM. The organic extracts were combined, dried over sodium sulfate, filtered, concentrated, and purified on a silica gel filter plug (DCM to 20:1 DCM/MeOH) to afford 4-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide. MS (ESI positive ion) m/z: 389 (M+1, 79Br), 391 (M+1, 81Br). Calcd. for C13H10BrClN2O3S: 388 (79Br), 390 (81Br).

1. customplaced in a preheated oil bath
2. concentrationconcentrated
3. additionpoured into a biphasic solution of water (40 mL) and DCM (50 mL)
4. customThe layers were separated
5. extractionthe aqueous phase was extracted with DCM
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. custompurified on a silica gel
10. filtrationfilter plug (DCM to 20:1 DCM/MeOH)