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

HRID 9324ノート

反応式

HRID 9324 の反応式
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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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, 6 H), 3.82 (s, 3 H), 6.87–6.93 (m, 2 H), 7.20–7.15 (m, 2 H), 7.37–7.32 (m, 1 H), 7.49–7.46 (m, 1 H), 7.63 (d, 1 H, J=1.14 Hz), 10.4 (s, 1 H); 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.

後処理

  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)

出典と根拠

ORDレコード
ord-50462c2ef19b45b9985f6de89953a1bc
出典データセット
uspto-grants-2006_08
特許番号
US07091234B2

反応ノート

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