Cesium carbonate → Methyl {4-[(butyl{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]-2-methylphenoxy}acetate

HRID 1269587ノート

反応式

HRID 1269587 の反応式
C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[CH2:47]([NH:51][CH2:52][C:53]1[CH:64]=[CH:63][C:56]([O:57][CH2:58][C:59]([O:61][CH3:62])=[O:60])=[C:55]([CH3:65])[CH:54]=1)[CH2:48][CH2:49][CH3:50].Br[C:67]1[CH:72]=[CH:71][CH:70]=[C:69]([C:73]2[CH:78]=[CH:77][C:76]([C:79]([F:82])([F:81])[F:80])=[CH:75][CH:74]=2)[N:68]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:47]([N:51]([CH2:52][C:53]1[CH:64]=[CH:63][C:56]([O:57][CH2:58][C:59]([O:61][CH3:62])=[O:60])=[C:55]([CH3:65])[CH:54]=1)[C:67]1[CH:72]=[CH:71][CH:70]=[C:69]([C:73]2[CH:78]=[CH:77][C:76]([C:79]([F:80])([F:82])[F:81])=[CH:75][CH:74]=2)[N:68]=1)[CH2:48][CH2:49][CH3:50]

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 184483252-Bromo-6-(4-(trifluoromethyl)phenyl)pyridineHCID 58622898Methyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate

生成物 1

HCID 58622857Methyl {4-[(butyl{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]-2-methylphenoxy}acetate収率 34.3%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒

反応条件

温度
80 °C

実験手順

Palladium (II) acetate (5.4 mg, 0.024 mmol) and (S)-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (22 mg, 0.036 mmol) in anhydrous toluene (1.2 mL) were stirred together at 70° C. in a sealed reactivial for 30 minutes. The vial was then allowed to attain room temperature before the methyl {4-[(butylamino)methyl]-2-methylphenoxy}acetate (96 mg, 0.36 mmol), 2-bromo-6-[4-(trifluoromethyl)phenyl]pyridine (90.6 mg, 0.3 mmol) and caesium carbonate (137 mg, 0.42 mmol) were added. The vial was then sealed and heated at 80° C. for 18 h. The reaction mixture was allowed to cool to room temperature, the reaction mixture filtered and the solvent removed in vacuo. Purification by SPE (Silica, 10 g) eluting 99:1–50:1 cyclohexane:EtOAc afforded the title compound as a colourless oil (50 mg).

後処理

  1. additionwere added
  2. customThe vial was then sealed
  3. temperatureto cool to room temperature
  4. filtrationthe reaction mixture filtered
  5. customthe solvent removed in vacuo
  6. customPurification by SPE (Silica, 10 g)
  7. washeluting 99:1–50:1 cyclohexane

出典と根拠

ORDレコード
ord-48fcca34f05546e092e3571a1f626f67
出典データセット
uspto-grants-2007_04
特許番号
US07199239B2

反応ノート

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