Potassium Carbonate → 5-(3-Methoxy-phenyl)-3,3-dimethyl-1,3-dihydro-indol-2-one

HRID 496678노트

반응식

HRID 496678 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6](=[O:11])[C:5]2([CH3:13])[CH3:12].[CH3:14][O:15][C:16]1[CH:17]=[C:18](B(O)O)[CH:19]=[CH:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C(COC)OC.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.CCOC(C)=O>[CH3:14][O:15][C:16]1[CH:21]=[C:20]([C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][C:6](=[O:11])[C:5]3([CH3:13])[CH3:12])[CH:19]=[CH:18][CH:17]=1

참가 물질

9

반응물 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 2734370(3-Methoxyphenyl)boronic acidHCID 120527965-bromo-3,3-dimethyl-2,3-dihydro-1H-indol-2-one

생성물 1

HCID 98601415-(3-Methoxy-phenyl)-3,3-dimethyl-1,3-dihydro-indol-2-one수율 31%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

실험 절차

5-bromo-1,3-dihydro-3,3-dimethyl-2H-indol-2-one (0.33 g, 1.38 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.094 g) were stirred under an atmosphere of nitrogen in dimethoxyethane (12 cm3). After 15 minutes, 3-methoxyphenylboronic acid (0.42 g, 2.76 mmol) was added, followed by potassium carbonate (1.15 g, 8.34 mmol) in water (5 cm3). The reaction was heated to reflux for 5 hours, and then cooled to room temperature. Saturated aqueous ammonium chloride and EtOAc were added and the mixture was filtered. The aqueous layer was extracted with EtOAc (×2), and the combined organic layers were dried (MgSO4), filtered, and evaporated. The residue was purified by column chromatography (SiO2, EtOAc:hexane 1:3) to afford 5-(3-methoxy-phenyl)-3,3-dimethyl-1,3-dihydro-indol-2-one (0.11 g, 31%), mp=157-158° C.; 1H NMR (DMSO-d6) δ 3.34 (s, 6H), 3.82 (s, 3H), 6.87-6.93 (m, 2H), 7.20-7.15 (m, 2H), 7.37-7.32 (m, 1H), 7.49-7.46 (m, 1H), 7.63 (d, 1H, J=1.14 Hz), 10.4 (s, 1H); MS (EI) m/z 266 (M−H)−; CHN calculated for C17H17NO2: C, 76.38; H, 6.41;N, 5.24; Found: C, 76.02; H, 6.49; N, 5.02.

후처리

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 5 hours
  3. filtrationthe mixture was filtered
  4. extractionThe aqueous layer was extracted with EtOAc (×2)
  5. dry with materialthe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified by column chromatography (SiO2, EtOAc:hexane 1:3)

출처 및 근거

ORD 기록
ord-89c95bcc866a42cfbd78d593c6762727
출처 데이터셋
uspto-grants-2005_09
특허 번호
US06946454B2

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