Ethyl Acrylate → 5-(4-Fluorophenyl)-3-(1-methylethyl)-1-(2-pyrimidinyl)-1H-pyrazole 2-propenoic acid, ethyl ester

HRID 1032452ノート

反応式

HRID 1032452 の反応式
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].Br[C:9]1[C:10]([CH:27]([CH3:29])[CH3:28])=[N:11][N:12]([C:21]2[N:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[C:13]=1[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1>CN(C=O)C.CCN(CC)CC.CCOCC.O.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[F:20][C:17]1[CH:18]=[CH:19][C:14]([C:13]2[N:12]([C:21]3[N:26]=[CH:25][CH:24]=[CH:23][N:22]=3)[N:11]=[C:10]([CH:27]([CH3:29])[CH3:28])[CH:9]=2)=[CH:15][CH:16]=1.[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3]

参加物

8

反応物 2

HCID 8821Ethyl AcrylateHCID 148513232-[4-bromo-5-(4-fluorophenyl)-3-(1-methylethyl)-1H-pyrazol-1-yl]pyrimidine

生成物 1

HCID 867442225-(4-Fluorophenyl)-3-(1-methylethyl)-1-(2-pyrimidinyl)-1H-pyrazole 2-propenoic acid, ethyl ester

試薬・触媒・溶媒 5

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒HCID 6228Dimethylformamide溶媒HCID 8471Triethylamine溶媒

実験手順

Ethyl acrylate (16.2 ml, 0.15 mol) and bis-(triphenylphosphine) palladium (II) chloride (0.84 g, 0.0012 mol) in DMF (75 ml) and Et3N (75 ml) was heated together at reflux under N2 with stirring until a homogeneous solution resulted. 2-[4-Bromo-5-(4-fluorophenyl))-3-(1-methylethyl)-1H-pyrazol-1-yl]pyrimidine (3) (10.8 g, 0.03 mol) was added and the resulting solution was heated at reflux for 24 hours, during which, an additional 1 mol % of catalyst was added. The mixture was then cooled to room temperature and diluted with ether and water. The organic layer was separated and washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting solid (10.4 g) was recrystallized from hexane/ethyl acetate, mp 155°-162° C.

後処理

  1. temperatureat reflux under N2
  2. customresulted
  3. temperaturethe resulting solution was heated
  4. temperatureat reflux for 24 hours, during which
  5. additionan additional 1 mol % of catalyst was added
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe resulting solid (10.4 g) was recrystallized from hexane/ethyl acetate, mp 155°-162° C.

出典と根拠

ORDレコード
ord-599e09fcfe9f4ea09233983333bc5570
出典データセット
uspto-grants-1990_09
特許番号
US04957971

反応ノート

読み込み中…