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

HRID 252730
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 252730
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
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Komponenten

7

Edukt 4

HCID 25953Cesium fluorideHCID 83681Tris(1,1-dimethylethyl)phosphineHCID 2809072-Acetamido-4-methylthiazoleHCID 86244443N-(2-bromopyridin-4-yl)benzenesulfonamide

Produkt 1

HCID 86620406N-[4-Methyl-5-(4-phenylsulfonylaminopyridin-2-yl)-1,3-thiazol-2-yl]acetamideAusbeute 13,4 %

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 167845palladium(II) acetateKatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

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.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-2ba2a44a4a134a01ac363582ebb2b736
Quelldatensatz
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07868188B2

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