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

HRID 17037

Reaktionsgleichung

Reaktionsgleichung von HRID 17037
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1Br)[C:8](=[O:11])[O:9][CH3:10].C(=O)([O-])[O-].[K+].[K+].[CH3:36][O:37][C:38]1[CH:43]=[CH:42][C:41]([CH3:44])=[CH:40][C:39]=1B(O)O.CC(C)=O.O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CC(C)=O.CCCCCC>[F:1][C:2]([F:29])([F:28])[C:3]1[CH:4]=[C:5]([CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=1)[CH2:6][N:7]([CH2:12][C:13]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:14]=1[C:39]1[CH:40]=[C:41]([CH3:44])[CH:42]=[CH:43][C:38]=1[O:37][CH3:36])[C:8](=[O:11])[O:9][CH3:10]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 2773485(2-Methoxy-5-methylphenyl)boronic acidHCID 18366337Propan-2-one--water (1/1)HCID 86615391Methyl [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-fluorobenzyl)carbamate

Produkt 1

HCID 11663709Methyl [3,5-bis(trifluoromethyl)benzyl][(4-fluoro-2'-methoxy-5'-methylbiphenyl-2-yl)methyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 21880519Acetone hexaneLösungsmittel

Versuchsvorschrift

A mixture of the Methyl [3,5-bis(trifluoromethyl)benzyl](2-bromo-5-fluorobenzyl)carbamate from Step B (0.02 g, 0.04 mmol), potassium carbonate (0.01 g, 0.08 mmol), 2-methoxy-5-methyl phenyl boronic acid (0.008 g, 0.05 mmol) and catalytic amount of palladium acetate (1 mg) in 4:1 acetone/water (2.5 ml) was heated to and maintained at reflux for 1 h. TLC analysis (acetone/hexane=5:95) showed no starting material. The solvent was removed under reduced pressure and the residue was extracted with methylene chloride (3×10 ml). The combined organic layers were washed with brine and dried over sodium sulfate. The title compound was obtained by preparative thin layer chromatography using acetone:hexane (5:95) as the eluant. 1H NMR (CDCl3, 500 MHz) δ 7.75 (s, 1H), 7.50 (s, 1H), 7.38 (s, 1H), 7.20 (m, 2H), 7.04 (m, 2H), 6.84 (s, 1H), 6.80 (m, 1H), 4.18-4.60 (m, 4H), 3.80 (s, 3H), 3.68 (s, 3H), 2.32 (s, 3H). LC-MS (M+1) 530.4 (4.43 min).

Aufarbeitung

  1. temperaturewas heated to and
  2. temperaturemaintained
  3. temperatureat reflux for 1 h
  4. customThe solvent was removed under reduced pressure
  5. extractionthe residue was extracted with methylene chloride (3×10 ml)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate

Quellen und Nachweise

ORD-Eintrag
ord-e8f5d7c40c2b4de1b70194922c1f07fc
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737295B2

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