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

HRID 1162469Notes

Reaction equation

[NH2:1][C:2]1[C:3]([Cl:9])=[N:4][CH:5]=[C:6]([Br:8])[CH:7]=1.[F:10][CH:11]([F:23])[O:12][C:13]1[CH:14]=[C:15]([S:19](Cl)(=[O:21])=[O:20])[CH:16]=[CH:17][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>N1C=CC=CC=1>[Br:8][C:6]1[CH:7]=[C:2]([NH:1][S:19]([C:15]2[CH:16]=[CH:17][CH:18]=[C:13]([O:12][CH:11]([F:10])[F:23])[CH:14]=2)(=[O:21])=[O:20])[C:3]([Cl:9])=[N:4][CH:5]=1

Participants

Conditions

Temperature: 25 °C

Procedure

A round bottomed flask was charged with 3-amino-5-bromo-2-chloropyridine (1.5 g, 7 mmol, Asymchem Laboratories, Inc. Morrisville, N.C.) and pyridine (20 mL). To this solution, 3-(difluoromethoxy)benzenesulfonyl chloride (2 mL, 8 mmol, Sigma-Aldrich Corporation, St. Louis, Mo.) was added dropwise and the solution was stirred at 25° C. for 18 h. The mixture was concentrated in vacuum and the residue was suspended in H2O. The white solid was collected by filtration and then suspended in methanol (50 mL). To this suspension, potassium carbonate (1.9 g, 14 mmol) was added, and the mixture was stirred at 25° C. for 20 h. The suspension was filtered and the filtrate was concentrated in vacuo. Purification by silica gel chromatography (10-50% EtOAC/Hexane) afforded the title compound (1.4 g, 47% yield) as a white solid. MS (ESI positive ion) m/z: 415 (M+1).

Workup

concentrationThe mixture was concentrated in vacuum
filtrationThe white solid was collected by filtration
stirringthe mixture was stirred at 25° C. for 20 h
filtrationThe suspension was filtered
concentrationthe filtrate was concentrated in vacuo
customPurification by silica gel chromatography (10-50% EtOAC/Hexane)

Sources & evidence

ORD record: ord-802972aa4ef6476fbc8ac4e733cbed38
Source dataset: uspto-grants-2010_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07820665B2

Reaction notes

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