Ethyl Acetoacetate → ethyl 4-(1-ethoxy-1,3-dioxobutan-2-yl)-7-o-tolyl-1H-indole-2-carboxylate

HRID 576269노트

반응식

HRID 576269 반응식
Cl[C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:6]2.[O:23]=[C:24]([CH3:31])[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27].C(P(C(C)(C)C)C1C=CC=CC=1C1C=CC=CC=1C)(C)(C)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:29]([O:28][C:26](=[O:27])[CH:25]([C:2]1[CH:10]=[CH:9][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[C:7]2[C:3]=1[CH:4]=[C:5]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[NH:6]2)[C:24](=[O:23])[CH3:31])[CH3:30]

참가 물질

7

반응물 4

HCID 8868Ethyl AcetoacetateHCID 62657Potassium Phosphate, TribasicHCID 27349372-(Di-tert-butylphosphino)-2'-methyl-1,1'-biphenylHCID 68936971ethyl 4-chloro-7-o-tolyl-1H-indole-2-carboxylate

생성물 1

HCID 68940072ethyl 4-(1-ethoxy-1,3-dioxobutan-2-yl)-7-o-tolyl-1H-indole-2-carboxylate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 1140Toluene용매

반응 조건

온도
93 °C

실험 절차

A mixture of ethyl 4-chloro-7-o-tolyl-1H-indole-2-carboxylate (EXAMPLE 166C) (0.93 g), ethyl 3-oxobutanoate (0.849 g), di-tert-butyl(2′-methylbiphenyl-2-yl)phosphine (0.093 mg), K3PO4 (3.46 g), and palladium(II) acetate (0.033 g) in toluene (8 mL) was degassed via vacuum/nitrogen cycle three times. The reaction mixture was heated at 93° C. for 14 hours. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was separated, and the aqueous layer was extracted with additional ethyl acetate. The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated. The residue was purified with flash chromatography on silica gel (ethyl acetate in hexanes) to give the title compound.

후처리

  1. customwas degassed via vacuum/nitrogen cycle three times
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with additional ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified with flash chromatography on silica gel (ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-b54334d1a42d44c6934b3283461651bd
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09035047B2

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