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

HRID 252730
ノート
印刷プレビュー

反応式

HRID 252730 の反応式
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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

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

生成物 1

HCID 86620406N-[4-Methyl-5-(4-phenylsulfonylaminopyridin-2-yl)-1,3-thiazol-2-yl]acetamide収率 13.4%

試薬・触媒・溶媒 2

HCID 167845
palladium(II) acetate
触媒
HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
150 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2ba2a44a4a134a01ac363582ebb2b736
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07868188B2

反応ノート

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