Carbon Dioxide → HCID 57736444, compound

HRID 1641689Notes

Reaction equation

HRID 1641689 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]([C:18]2[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=2[F:25])[S:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.CCCCCC.C([Li])CCC.[C:37](=[O:39])=[O:38]>C1(C)C=CC=CC=1>[F:25][C:19]1[CH:20]=[CH:21][C:22]([F:24])=[CH:23][C:18]=1[CH:9]([S:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)[C:5]1[C:6]([CH3:8])=[CH:7][C:2]([C:37]([OH:39])=[O:38])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 8058HexaneHCID 57736453HCID 57736453, compoundHCID 178418339Butyllithium

Product 1

HCID 57736444HCID 57736444, compoundYield 64%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 2-bromo-5-[(2,5-difluorophenyl)[(4-fluorophenyl)thio]methyl ]-4-methylpyridine (1.39 g, 3.28 mmol) obtained in Example 10 in toluene (60 ml), a hexane solution of n-butyllithium (1.54 M, 2.55 ml, 3.93 mmol) was added in an argon atmosphere at −78° C. After stirring for 1 hour at the same temperature, carbon dioxide was bubbled thereinto the mixture. The reaction mixture was allowed to warm to room temperature over 2 hours, subsequently 0.1 N hydrochloric acid was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with methylene chloride:methanol=10:1 was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of ethanol, diethyl ether and hexane, and was collected by filtration, to obtain the title compound (815 mg, 2.09 mmol, 64%) as a white solid.

Workup

  1. customwas bubbled
  2. additionsubsequently 0.1 N hydrochloric acid was added
  3. extractionthe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe fraction obtained from an elution with methylene chloride
  8. concentrationmethanol=10:1 was concentrated under reduced pressure
  9. washthe resulting residue was washed with a mixed solvent of ethanol, diethyl ether and hexane
  10. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-908be6f341b54d8d945137fae6de5297
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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