Sodium Carbonate → 2'-({5-[3,5-Bis(trifluoromethyl)phenyl]-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-methoxy-4'-(trifluoromethyl)biphenyl-3-carbaldehyde

HRID 1028635

Reaktionsgleichung

Reaktionsgleichung von HRID 1028635
[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3I)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH:33]([C:35]1[CH:36]=[CH:37][C:38]([O:44][CH3:45])=[C:39](B(O)O)[CH:40]=1)=[O:34].C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC=CC=1.C(O)C.O.CCOC(C)=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>[F:1][C:2]([F:32])([F:31])[C:3]1[CH:4]=[C:5]([CH:13]2[O:17][C:16](=[O:18])[N:15]([CH2:19][C:20]3[CH:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:21]=3[C:37]3[C:38]([O:44][CH3:45])=[CH:39][CH:40]=[C:35]([CH:33]=[O:34])[CH:36]=3)[CH2:14]2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 27343675-Formyl-2-methoxyphenylboronic acidHCID 591352395-[3,5-Bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]1,3-oxazolidin-2-one

Produkt 1

HCID 866034382'-({5-[3,5-Bis(trifluoromethyl)phenyl]-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-methoxy-4'-(trifluoromethyl)biphenyl-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 8857Ethyl AcetateLösungsmittelHCID 66847609Benzene ethanol waterLösungsmittel

Versuchsvorschrift

A mixture of 5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one (Example 66, 50 mg; 0.0858 mmol), 5-formyl-2-methoxyphenyl boronic acid (46 mg; 0.257 mmol), tetrakis(triphenylphosphine)palladium (0) (12 mg; 0.0103 mmol), and sodium carbonate (74 mg) in benzene/ethanol/water (2.8/0.4/1.2 mL) was heated at reflux for 60 h. The reaction was diluted with EtOAc (30 mL) and washed successively with H2O (10 mL) and brine (10 mL), dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (0-50% EtOAc/hexanes gradient) to afford 2′-({5-[3,5-bis(trifluoromethyl)phenyl]-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-methoxy-4′-(trifluoromethyl)biphenyl-3-carbaldehyde as a yellow oil. LCMS=592.1 (M+1)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers): δ 9.98 (s, 1 H), 7.99-7.96 (m, 1 H), 7.90 (s, 1 H), 7.75 (s, 2 H), 7.69-7.64 (m, 2 Hz), 7.53 (s, 1 H), 7.41-7.38 (m, 1 H), 7.17-7.14 (m, 1 H), 5.37 (t, J=8.2 Hz, 1 H), 4.59 (d, J=15.3 Hz, 1 H), 4.37 (d, J=15.6 Hz, 1 H), 3.92 (s, 3 H), 3.67-3.64 (m, 1 Hz), 3.19-3.16 (m, 1 H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 60 h
  3. washwashed successively with H2O (10 mL) and brine (10 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash silica gel chromatography (0-50% EtOAc/hexanes gradient)

Quellen und Nachweise

ORD-Eintrag
ord-ca8d4ef2600143819eb2c0111dc22ade
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735435B2

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