Cesium fluoride → N-[4-Methyl-5-(4-phenylsulfonylaminopyridin-2-yl)-1,3-thiazol-2-yl]acetamide

HRID 252730Notes

Reaction equation

Br[C:2]1[CH:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][N:3]=1.[C:18]([NH:21][C:22]1[S:23][CH:24]=[C:25]([CH3:27])[N:26]=1)(=[O:20])[CH3:19].[F-].[Cs+].C(P(C(C)(C)C)C(C)(C)C)(C)(C)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CS(C)=O>[CH3:27][C:25]1[N:26]=[C:22]([NH:21][C:18](=[O:20])[CH3:19])[S:23][C:24]=1[C:2]1[CH:7]=[C:6]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)(=[O:11])=[O:10])[CH:5]=[CH:4][N:3]=1

Participants

Conditions

Temperature: 150 °C

Procedure

A mixture of N-(2-bromopyridin-4-yl)benzenesulfonamide (700 mg), 2-acetamido-4-methylthiazole (384 mg), palladium(II) acetate (41 mg), caesium fluoride (1.01 g), tri-tert-butylphosphine (0.34M solution in hexane, 1.06 mL) and DMSO (20 mL) was purged with nitrogen. The resultant mixture was heated to 150° C. for 5 hours under an atmosphere of nitrogen. The bulk of the DMSO was evaporated and the residue was treated with water (40 mL). Water was decanted from the resultant gum which was purified by column chromatography on silica using a solvent gradient of 2% to 5% methanol in dichloromethane as eluent. There was thus obtained the title compound as a solid (116 mg); 1H NMR Spectrum: (DMSOd6) 2.14 (s, 3H), 2.44 (s, 3H), 6.93 (d, 1H), 7.32 (s, 1H), 7.60-7.70 (m, 3H), 7.91 (m, 2H), 8.29 (d, 1H), 11.25 (s, 1H), 12.13 (s, 1H); Mass Spectrum: M+H+ 389.

Workup

customwas purged with nitrogen
customThe bulk of the DMSO was evaporated
additionthe residue was treated with water (40 mL)
customWater was decanted from the resultant gum which
customwas purified by column chromatography on silica using a solvent gradient of 2% to 5% methanol in dichloromethane as eluent

Sources & evidence

ORD record: ord-2ba2a44a4a134a01ac363582ebb2b736
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07868188B2

Reaction notes

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