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Water → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-[3-(2-oxo-1,3-oxazolin-3-yl)-1-propynyl]-3-hydroxy-3-(2-chlorophenyl)oxindole

HRID 1369106
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HRID 1369106 반응식
[CH2:1]([N:3]([CH2:29][CH3:30])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=[C:12](I)[CH:13]=2)[C:8]([OH:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[C:7]1=[O:28])[CH3:2].[O:31]=[C:32]1[N:36]([CH2:37][C:38]#[CH:39])[CH:35]=[CH:34][O:33]1.O.C([O-])(O)=O.[Na+]>C(N(CC)CC)C.[Cu]I.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([N:3]([CH2:29][CH3:30])[CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[C:10]([C:16]([F:19])([F:18])[F:17])[CH:11]=[C:12]([C:39]#[C:38][CH2:37][N:36]3[CH:35]=[CH:34][O:33][C:32]3=[O:31])[CH:13]=2)[C:8]([OH:27])([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[Cl:26])[C:7]1=[O:28])[CH3:2]
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참가 물질

8

반응물 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 119878593-(2-Oxo-1,3-oxazolin-3-yl)-1-propyneHCID 129902161-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-chlorophenyl)oxindole

생성물 1

HCID 185185761-(2-Diethylaminoethyl)-4-trifluoromethyl-6-[3-(2-oxo-1,3-oxazolin-3-yl)-1-propynyl]-3-hydroxy-3-(2-chlorophenyl)oxindole수율 935.3%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 178418476HCID 178418476, 화합물촉매HCID 8471Triethylamine용매

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온도
50 °C

실험 절차

A mixture of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-chlorophenyl)oxindole (796 mg, 0.144 mmol), 3-(2-oxo-1,3-oxazolin-3-yl)-1-propyne (464 mg, 0.371 mmol), CuI (10.8 mg, 0.0567 mmol), and (PPh3)2PdCl2 (18.6 mg, 0.0265 mmol) in triethylamine (1 mL) was stirred for 4.5 h at 50° C. Water and sat. aqueous NaHCO3 were added and the mixture was extracted with ethyl acetate. The extracts were dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography with 80:1 to 50:1 chloroform/methanol to give the title compound (738 mg). The compound was dissolved in dioxane (2 mL) and 4 N HCl in dioxane (1 mL) was added. The solvent was evaporated azeotropically with toluene. The residual solid was washed with ether and dried in vacuo to give the hydrochloride (528 mg, 63%).

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. dry with materialThe extracts were dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatography with 80:1 to 50:1 chloroform/methanol

출처 및 근거

ORD 기록
ord-9e4def75de134fc79512c931a790fd92
출처 데이터셋
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06576656B1

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