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Ethanol → 1-(2-Diethylaminoethyl)-4-trifluoromethyl-6-ethoxycarbonyl-3-hydroxy-3-(2-naphthyl)oxindole

HRID 1369095
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HRID 1369095 반응식
[CH2:1]([N:3]([CH2:32][CH3:33])[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:30])([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[C:7]1=[O:31])[CH3:2].C(N([CH2:39][CH3:40])CC)C.C(O)C.[C:44]([O-])([OH:46])=[O:45].[Na+]>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.C1(C)C=CC=CC=1>[CH2:1]([N:3]([CH2:32][CH3:33])[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:44]([O:46][CH2:39][CH3:40])=[O:45])[CH:13]=2)[C:8]([OH:30])([C:20]2[CH:29]=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=2)[C:7]1=[O:31])[CH3:2]
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7

반응물 4

HCID 702EthanolHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 118278961-(2-Diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-naphthyl)oxindole

생성물 1

HCID 185186261-(2-Diethylaminoethyl)-4-trifluoromethyl-6-ethoxycarbonyl-3-hydroxy-3-(2-naphthyl)oxindole

시약·촉매·용매 2

HCID 178418476
HCID 178418476, 화합물
촉매
HCID 1140Toluene용매

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온도
60 °C

실험 절차

A mixture of 1-(2-diethylaminoethyl)-4-trifluoromethyl-6-iodo-3-hydroxy-3-(2-naphthyl)oxindole of Example 48 (300 mg, 0.527 mmol), triethylamine (0.15 mL, 1.08 mmol), and (PPh3)2PdCl2 (40 mg, 0.087 mmol) in a mixed solvent of ethanol (1.5 mL) and toluene (1.5 mL) was stirred for 7 h at 60° C. under CO atmosphere. Sat. aqueous NaHCO3 was 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 50:1 chloroform/methanol to give the title compound (273 mg, quant.).

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 50:1 chloroform/methanol

출처 및 근거

ORD 기록
ord-2f7c5d2f232940caae24afb13084a19d
출처 데이터셋
uspto-grants-2003_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06576656B1

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