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

反応式

HRID 1028635 の反応式
[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

参加物

7

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 178418397HCID 178418397、化合物触媒HCID 8857Ethyl Acetate溶媒HCID 66847609Benzene ethanol water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ca8d4ef2600143819eb2c0111dc22ade
出典データセット
uspto-grants-2014_05
特許番号
US08735435B2

関連ノート

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