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Water → methyl 3-(4-(2,3-dihydro-1H-inden-2-yloxy)-2-cyano-5-(1-methyl-1H-indazol-5-yl)phenyl)propanoate

HRID 2194950
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HRID 2194950 반응식
[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[C:16]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[N:21]=[CH:20]3)=[CH:15][C:14]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[C:13](OS(C(F)(F)F)(=O)=O)[CH:12]=1.C(=O)([O-])[O-].[Na+].[Na+].O.C(OCC)(=O)C.[CH3:54][N:55](C)C(=O)C>[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[C-]#N.[K+].[K+].[K+].[K+].[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][CH:2]1[O:10][C:11]1[C:16]([C:17]2[CH:18]=[C:19]3[C:23](=[CH:24][CH:25]=2)[N:22]([CH3:26])[N:21]=[CH:20]3)=[CH:15][C:14]([CH2:27][CH2:28][C:29]([O:31][CH3:32])=[O:30])=[C:13]([C:54]#[N:55])[CH:12]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

8

반응물 5

HCID 962WaterHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 86640868Methyl 3-(4-(2,3-dihydro-1H-inden-2-yloxy)-5-(1-methyl-1H-indazol-5-yl)-2-(trifluoromethylsulfonyloxy)phenyl)propanoate

생성물 1

HCID 66877829
methyl 3-(4-(2,3-dihydro-1H-inden-2-yloxy)-2-cyano-5-(1-methyl-1H-indazol-5-yl)phenyl)propanoate

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 9605257Potassium Ferrocyanide촉매

실험 절차

A solution of Intermediate 6 (30 mg) in N,N-dimethylacetamide (1 ml) was added with K4[Fe(CN)6].3H2O (6.6 mg, Ald), sodium carbonate (5.5 mg), and palladium acetate (1.1 mg, WAKO), and stirred at 120° C. for 5 hours. The reaction mixture was added with water (3 ml), and ethyl acetate (3 ml×2) for extraction, and then successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine, the organic layer was dried, and then the solvent was evaporated under reduced pressure. The residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1), and the solvent was evaporated under reduced pressure by using a rotary evaporator to obtain the title compound (yield: 10 mg).

후처리

  1. washsuccessively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine
  2. customthe organic layer was dried
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by column chromatography (Yamazen, n-hexane:ethyl acetate=3:1)
  5. customthe solvent was evaporated under reduced pressure
  6. customa rotary evaporator

출처 및 근거

ORD 기록
ord-3daffcc95df54158b0ac143d7552d31f
출처 데이터셋
uspto-grants-2012_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08334314B2

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