Potassium Carbonate → 4-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide

HRID 1162473Notes

Reaction equation

[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[C:10]([C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1)(=[O:12])[CH3:11].C([O-])([O-])=O.[K+].[K+]>N1C=CC=CC=1>[C:10]([C:13]1[CH:14]=[CH:15][C:16]([S:19]([NH:1][C:2]2[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=2)(=[O:21])=[O:20])=[CH:17][CH:18]=1)(=[O:12])[CH3:11]

Participants

Conditions

Temperature: 100 °C

Procedure

To a 150 mL, round-bottomed flask was added 3-amino-5-bromo-2-chloropyridine (1 g, 5 mmol, Asymchem Laboratories, Morrisville, N.C.) and pyridine(10 mL). To this solution, 4-acetylbenzenesulfonyl chloride (2 g, 10 mmol, Sigma-Aldrich Corporation, St. Louis, Mo.) was added, the mixture was stirred at 25° C. for 15 h and at 100° C. for additional 2 h. The mixture was concentrated in high vacuo. The result brown oil was suspended in methanol (200 mL)-H2O (5 mL). To this suspension, K2CO3 (2 g, 14.4 mmol) was added and the mixture was stirred at 25° C. for 15 h. The methanol was removed in vacuum; the residue was treated with H2O. Filtration provided 4-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide (0.5 g) as a brown solid. The filtrate was extracted by MeOH-DCM (10%) to provide additional 1.1 g of 4-acetyl-N-(5-bromo-2-chloropyridin-3-yl)benzenesulfonamide as a white solid. MS (ESI positive ion) m/z: 391 (M+1). 1H NMR (400 MHz, DMSO-d6): δ ppm 2.57 (s, 3H), 7.51-7.56 (m, 2H), 7.81 (d, J=8.41 Hz, 2H), 7.98 (d, J=8.41 Hz, 2H).

Workup

concentrationThe mixture was concentrated in high vacuo
stirringthe mixture was stirred at 25° C. for 15 h
customThe methanol was removed in vacuum
additionthe residue was treated with H2O
filtrationFiltration

Sources & evidence

ORD record: ord-304e0cb8bf8541da8b87882b4e7f5a4a
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820665B2

Reaction notes

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