Carbon Dioxide → HCID 18326214, compound

HRID 1250511Notes

Reaction equation

HRID 1250511 reaction equation
Br[C:2]1[CH:7]=[C:6]([N:8]([CH3:16])[CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:5]=[C:4]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:3]=1.CCCCCC.[Li]CCCC.[C:39](=[O:41])=[O:40]>C(OCC)C>[CH3:16][N:8]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:6]1[CH:5]=[C:4]([O:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=2)[N:3]=[C:2]([C:39]([OH:41])=[O:40])[CH:7]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8058HexaneHCID 21249824HCID 21249824, compoundHCID 178418339Butyllithium

Product 1

HCID 18326214HCID 18326214, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

2.00 g (0.0046 mol) of 2-bromo-4-{methyl(phenylmethyl)amino}-6-{3-(trifluoromethyl)phenoxy} pyridine was dissolved in about 100 ml of diethyl ether. While cooling the obtained suspension in a dry ice-acetone bath in an argon atmosphere, 2.2 ml of a 1.6M-hexane solution of BuLi (0.0023×1.5 mol) was added thereto, followed by stirring the suspension for about 10 minutes. After an interior of reactor was replaced with carbon dioxide gas, the reaction solution was removed from the bath and stirred at room temperature for about one hour. The reaction solution was mixed with about 10 ml of a 1N-HCl aqueous solution, and then distributed in ethyl acetate-water, followed by washing with saturated brine. The organic phase of the obtained solution was dried with anhydrous sodium sulfate, concentrated and subjected to silica gel column chromatography (eluting solution: ethyl acetate/hexane) to remove a main fraction therefrom. The fraction was concentrated, thereby obtaining an aimed product.

Workup

  1. additionwas added
  2. customthe reaction solution was removed from the bath
  3. stirringstirred at room temperature for about one hour
  4. additionThe reaction solution was mixed with about 10 ml of a 1N-HCl aqueous solution
  5. washby washing with saturated brine
  6. dry with materialThe organic phase of the obtained solution was dried with anhydrous sodium sulfate
  7. concentrationconcentrated
  8. washsubjected to silica gel column chromatography (eluting solution: ethyl acetate/hexane)
  9. customto remove a main fraction
  10. concentrationThe fraction was concentrated

Sources & evidence

ORD record
ord-bf316694295d49818853c17ca4a84797
Source dataset
uspto-grants-2002_01
Patent number
US06339045B1

Reaction notes

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