Diisopropylethylamine → HCID 22600462, compound

HRID 1784152Notes

Reaction equation

HRID 1784152 reaction equation
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

Participants

6

Reactant 3

HCID 81531Diisopropylethylamine2×HCID 113349532-(2-Methoxy-ethoxymethyl)-6-trifluoromethyl-nicotinic acid2×HCID 57591513HCID 57591513, compound

Product 1

HCID 22600462HCID 22600462, compound

Reagents, catalysts & solvents 2

HCID 3007855ZincchlorideCatalyst2×HCID 7964ChlorobenzeneSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-490092c910054855818fdd351ad58b33
Source dataset
uspto-grants-2009_03
Patent number
US07501544B2

Reaction notes

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