Methyl 2-acetamidoacrylate → 2-Acetylamino-3-(2-[1,3]dioxan-2-yl-3-fluoro-phenyl)-acrylic acid methyl ester

HRID 2245284ノート

反応式

HRID 2245284 の反応式
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4](I)[C:3]=1[CH:9]1[O:14][CH2:13][CH2:12][CH2:11][O:10]1.[CH3:15][O:16][C:17](=[O:24])[C:18]([NH:20][C:21](=[O:23])[CH3:22])=[CH2:19].C(=O)(O)[O-].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[CH3:15][O:16][C:17](=[O:24])[C:18]([NH:20][C:21](=[O:23])[CH3:22])=[CH:19][C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[C:3]=1[CH:9]1[O:14][CH2:13][CH2:12][CH2:11][O:10]1

参加物

7

反応物 3

HCID 98644Methyl 2-acetamidoacrylateHCID 516892Sodium BicarbonateHCID 685501032-(2-Fluoro-6-iodo-phenyl)-[1,3]dioxane

生成物 1

HCID 685501862-Acetylamino-3-(2-[1,3]dioxan-2-yl-3-fluoro-phenyl)-acrylic acid methyl ester収率 12.4%

試薬・触媒・溶媒 3

HCID 70681Tetrabutylammonium Chloride触媒HCID 167845palladium(II) acetate触媒HCID 6228Dimethylformamide溶媒

実験手順

A DMF (10 ml) solution of 2-(2-fluoro-6-iodo-phenyl)-[1,3]dioxane (1.85 g, 6 mmol), 2-acetylamino-acrylic acid methyl ester (906 mg, 6.33 mmol), sodium bicarbonate (1.26 g, 15 mmol), tetrabutyl ammonium chloride (1.35 g, 4.86 mmol) and palladium (II) acetate (52 mg, 0.23 mmol) is heated at 90° C. for 1.8 hours. The reaction mixture is poured onto water and the aqueous phase is extracted with ethylacetate. The organic layer is washed with brine and dried over MgSO4 and evaporated. The crude product is purified by chromatography (CH2Cl2/MeOH, 95/5) to afford the desired compound (240 mg). MS (ES+): m/e=346.3, (MNa+)

後処理

  1. additionThe reaction mixture is poured onto water
  2. extractionthe aqueous phase is extracted with ethylacetate
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. customevaporated
  6. customThe crude product is purified by chromatography (CH2Cl2/MeOH, 95/5)

出典と根拠

ORDレコード
ord-381a067d5259455dae0a8904179e7689
出典データセット
uspto-grants-2010_03
特許番号
US07683075B2

反応ノート

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