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

HRID 2245284노트

반응식

HRID 2245284 반응식
[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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 70681Tetrabutylammonium Chloride촉매HCID 167845palladium(II) acetate촉매HCID 6228Dimethylformamide용매

실험 절차

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+)

후처리

  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)

출처 및 근거

ORD 기록
ord-381a067d5259455dae0a8904179e7689
출처 데이터셋
uspto-grants-2010_03
특허 번호
US07683075B2

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