Potassium Carbonate → Methyl [3,5-bis(trifluoromethyl)benzyl]{[2'-methoxy-5'-methyl-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

HRID 217479

Reaktionsgleichung

Reaktionsgleichung von HRID 217479
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[CH:15][C:14]=1I)[C:8](=[O:11])[O:9][CH3:10].[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][C:36]=1B(O)O.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C)=O.O>[CH3:10][O:9][C:8](=[O:11])[N:7]([CH2:6][C:5]1[CH:4]=[C:3]([C:2]([F:32])([F:31])[F:1])[CH:26]=[C:25]([C:27]([F:28])([F:29])[F:30])[CH:24]=1)[CH2:12][C:13]1[CH:18]=[C:17]([C:19]([F:21])([F:22])[F:20])[CH:16]=[CH:15][C:14]=1[C:36]1[CH:37]=[C:38]([CH3:41])[CH:39]=[CH:40][C:35]=1[O:34][CH3:33]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 2773485(2-Methoxy-5-methylphenyl)boronic acidHCID 59343876Methyl [3,5-bis(trifluoromethyl)benzyl](2-iodo-5-trifluoromethyl-benzyl)carbamate

Produkt 1

HCID 11261706Methyl [3,5-bis(trifluoromethyl)benzyl]{[2'-methoxy-5'-methyl-4-(trifluoromethyl)biphenyl-2-yl]methyl}carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 18366337Propan-2-one--water (1/1)Lösungsmittel

Versuchsvorschrift

A mixture of methyl[3,5-bis(trifluoromethyl)benzyl][2-iodo-5-(trifluoromethyl)benzyl]carbamate (0.10 g, 0.17 mmol) from Example 5, and 2-methoxy-5-methylphenyl boronic acid (0.034 g, 0.2 mmol), palladium acetate (0.0038 g, 0.017 mmol) and potassium carbonate (0.047 g, 0.34 mmol) in 4:1 acetone/water (10 ml) was heated and maintained at reflux for 1 h. The color of the solution turned dark. Acetone was removed and the residue was extracted with methylene chloride (3×10 ml). The combined organic layers were washed with water, then brine, and dried over sodium sulfate. The title compound was obtained as a colorless oil by preparative thin layer chromatography using acetone/hexane (5:95) as the eluant. 1H NMR (CDCl3, 500 MHz): δ 7.73 (s, 1H), 7.58 (d, J=8.5 Hz, 1H), 7.47 (s, 2H), 7.35 (m, 1H), 7.32 (d, J=8.0 Hz, 1H), 7.19 (m, 1H), 6.85 (m, 21-1), 4.23-4.36 (m, 4H), 3.79 (m, 3H), 3.68 (s, 3H), 2.25 (s, 3H). LC-MS (M+1): 580.0 (4.61 min).

Aufarbeitung

  1. temperaturewas heated
  2. temperaturemaintained
  3. temperatureat reflux for 1 h
  4. customAcetone was removed
  5. extractionthe residue was extracted with methylene chloride (3×10 ml)
  6. washThe combined organic layers were washed with water
  7. dry with materialbrine, and dried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-ae18445d747649edbc5b57829840b1d7
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193365B2

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