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

HRID 1269586ノート

反応式

HRID 1269586 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:67]=[CH:66][C:56]([O:57][C:58]([CH3:65])([CH3:64])[C:59]([O:61][CH2:62][CH3:63])=[O:60])=[C:55]([CH3:68])[CH:54]=1)[CH2:48][CH2:49][CH3:50].Br[C:70]1[CH:75]=[CH:74][CH:73]=[C:72]([C:76]2[CH:81]=[CH:80][C:79]([C:82]([F:85])([F:84])[F:83])=[CH:78][CH:77]=2)[N:71]=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:67]=[CH:66][C:56]([O:57][C:58]([CH3:65])([CH3:64])[C:59]([O:61][CH2:62][CH3:63])=[O:60])=[C:55]([CH3:68])[CH:54]=1)[C:70]1[CH:75]=[CH:74][CH:73]=[C:72]([C:76]2[CH:81]=[CH:80][C:79]([C:82]([F:83])([F:85])[F:84])=[CH:78][CH:77]=2)[N:71]=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 18448412Ethyl 2-{4-[(butylamino)methyl]-2-methylphenoxy}-2-methylpropanoate

生成物 1

HCID 18448411Ethyl 2-{4-[(butyl{6-[4-(trifluoromethyl)phenyl]pyridin-2-yl}amino)methyl]-2-methylphenoxy}-2-methylpropanoate収率 42.6%

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 (1.4 mg, 0.006 mmol) and (S)-2,2′-bis(diphenylphosphino)-1,1′-binapthyl (5.9 mg, 0.0095 mmol) in anhydrous toluene (0.32 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 ethyl 2-{4-[(butylamino)methyl]-2-methylphenoxy}-2-methylpropanoate (29 mg, 0.095 mmol), 2-bromo-6-[4-(trifluoromethyl)phenyl]pyridine (24 mg, 0.08 mmol) and caesium carbonate (36 mg, 0.11 mmol) were added. The vial was then sealed and heated at 80° C. for 18 h, then allowed to cool to room temperature the reaction mixture filtered and the solvent removed in vacuo. Purification by SPE (Silica, 10 g) eluting with 99:1 cyclohexane:EtOAc afforded the title compound as a colourless oil (18 mg).

後処理

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

出典と根拠

ORDレコード
ord-29a313d2c79e4e6ab81cfa0fb3215033
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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