Carbon Dioxide → HCID 18326214, compound

HRID 1531641Notes

Reaction equation

HRID 1531641 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.C([Li])CCC.[C:33](=[O:35])=[O:34].Cl>C(OCC)C.C(OCC)(=O)C.O>[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:33]([OH:35])=[O:34])[CH:7]=1

Participants

7

Reactant 4

HCID 280Carbon DioxideHCID 313Hydrochloric AcidHCID 21249824HCID 21249824, compoundHCID 178418339Butyllithium

Product 1

HCID 18326214HCID 18326214, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 22728543Water ethylacetateSolvent

Procedure

2-bromo-4-[methyl(phenylmethyl)amino]-6-[3-(trifluoromethyl)phenoxy] pyridine (6.38 g, 0.0146 mol) was dissolved in about 300 ml of diethyl ether. While cooling in a dry ice-acetone bath in an argon atmosphere, the obtained solution was mixed with n-butyl lithium [10 ml (ca. 1.63 M in hexane solution), 0.0146×1.1 mol] and then stirred for about 10 minutes. After the interior of the reactor was replaced with a carbon dioxide gas, the solution was removed from the bath and stirred at room temperature for about one hour. The obtained reaction solution was mixed with about 30 ml of a 1 N aqueous hydrochloric acid solution, distributed in ethyl acetate-water, and then washed with saturated brine. The organic phase separated from the solution was dried with anhydrous sodium sulfate, concentrated, and then purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), thereby obtaining an aimed product.

Workup

  1. temperatureWhile cooling in a dry ice-acetone bath in an argon atmosphere
  2. customthe solution was removed from the bath
  3. stirringstirred at room temperature for about one hour
  4. customThe obtained reaction solution
  5. washwashed with saturated brine
  6. customThe organic phase separated from the solution
  7. dry with materialwas dried with anhydrous sodium sulfate
  8. concentrationconcentrated
  9. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)

Sources & evidence

ORD record
ord-0ceb436eb5c64c19b8071abbcaf25f9b
Source dataset
uspto-grants-2001_03
Patent number
US06200933B1

Reaction notes

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