Diisopropylethylamine → HCID 22600462, 화합물

HRID 1784152노트

반응식

HRID 1784152 반응식
Br[C:2]1[CH:8]2[CH2:9][CH:5]([CH2:6][CH2:7]2)[C:4](=[O:10])[CH:3]=1.[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16][C:17]1[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20].CCN(C(C)C)C(C)C>ClC1C=CC=CC=1.[Cl-].[Cl-].[Zn+2]>[CH3:11][O:12][CH2:13][CH2:14][O:15][CH2:16][C:17]1[C:18]([C:19]([O:21][C:2]2[CH:8]3[CH2:9][CH:5]([CH2:6][CH2:7]3)[C:4](=[O:10])[CH:3]=2)=[O:20])=[CH:22][CH:23]=[C:24]([C:26]([F:29])([F:27])[F:28])[N:25]=1

참가 물질

6

반응물 3

HCID 81531Diisopropylethylamine2회HCID 113349532-(2-Methoxy-ethoxymethyl)-6-trifluoromethyl-nicotinic acid2회HCID 57591513HCID 57591513, 화합물

생성물 1

HCID 22600462HCID 22600462, 화합물

시약·촉매·용매 2

HCID 3007855Zincchloride촉매2회HCID 7964Chlorobenzene용매

실험 절차

A mixture of 27 g of a 6.2% solution of 4-bromobicyclo[3.2.1]oct-3-en-2-one (Preparation Example P1) in chlorobenzene, 110 mg of ZnCl2, 2.34 g of 2-methoxyethoxymethyl-6-trifluoromethylnicotinic acid and 1.2 g of Hünig's base is stirred at room temperature under a nitrogen atmosphere until a dark-brown solution is formed. The reaction mixture is then maintained under moderate reflux for 19 hours in an oil bath, with stirring. The mixture is then divided into 2 portions. To one portion there are added a further 1.12 g of 2-methoxyethoxymethyl-6-trifluoromethylnicotinic acid, 0.06 g of ZnCl2 and 0.6 g of Hünig's base. The reaction mixture is then maintained under moderate reflux for 12 hours in an oil bath, with stirring. The solution is then washed twice with 0.1M hydrochloric acid (20 ml each time) and twice with water (20 ml each time). After drying the organic solution using magnesium sulfate and concentrating in vacuo, 3.9 g of 4-(2-methoxyethoxymethyl-6-trifluoromethyl-pyridin-3-ylcarbonyloxy)-bicyclo[3.2.1]oct-3-en-2-one are obtained in the form of a brown oil.

후처리

  1. customis formed
  2. temperatureThe reaction mixture is then maintained
  3. temperatureunder moderate reflux for 19 hours in an oil bath
  4. stirringwith stirring
  5. temperatureThe reaction mixture is then maintained
  6. temperatureunder moderate reflux for 12 hours in an oil bath
  7. stirringwith stirring
  8. washThe solution is then washed twice with 0.1M hydrochloric acid (20 ml each time) and twice with water (20 ml each time)
  9. customAfter drying the organic solution
  10. concentrationconcentrating in vacuo, 3.9 g of 4-(2-methoxyethoxymethyl-6-trifluoromethyl-pyridin-3-ylcarbonyloxy)-bicyclo[3.2.1]oct-3-en-2-one
  11. customare obtained in the form of a brown oil

출처 및 근거

ORD 기록
ord-490092c910054855818fdd351ad58b33
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07501544B2

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