Water → HCID 57736502, compound

HRID 1641712Notes

Reaction equation

HRID 1641712 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]([C:17]2[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:18]=2[F:24])[S:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:4][N:3]=1.C([Li])CCC.CN(C)[CH:32]=[O:33].O>C1(C)C=CC=CC=1>[F:24][C:18]1[CH:19]=[CH:20][C:21]([F:23])=[CH:22][C:17]=1[CH:9]([S:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:5]1[C:6]([CH3:8])=[CH:7][C:2]([CH:32]=[O:33])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 57736432HCID 57736432, compoundHCID 178418339Butyllithium

Product 1

HCID 57736502HCID 57736502, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of 2-bromo-5-[(2,5-difluorophenyl)(phenylthio)methyl]-4-methyl pyridine (1.2 g, 3.0 mmol) in toluene (30 ml) was cooled to −78° C., and n-butyllithium (1.54 M hexane solution, 2.5 ml, 3.9 mmol) was added in an argon atmosphere. After stirring for 10 minutes at the same temperature, the mixture was allowed to warm to −40° C., stirred for 30 minutes, and cooled again to −78° C., and N,N-dimethylformamide (302 μl, 3.9 mmol) was added thereto. After stirring for 30 minutes at the same temperature, water was added to the mixture, and the mixture was extracted twice with ethyl acetate. The combined organic layer was washed with saturated brine, subsequently dried over anhydrous sodium sulfate, and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was subjected to flash silica gel column chromatography. The fraction obtained from an elution with hexane:ethyl acetate=93:7 was concentrated under reduced pressure to obtain the title compound mg, 0.70 mmol, 25%) as a colorless oily substance.

Workup

  1. stirringstirred for 30 minutes
  2. temperaturecooled again to −78° C.
  3. additionwas added to the mixture
  4. extractionthe mixture was extracted twice with ethyl acetate
  5. washThe combined organic layer was washed with saturated brine
  6. dry with materialsubsequently dried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe fraction obtained from an elution with hexane
  10. concentrationethyl acetate=93:7 was concentrated under reduced pressure

Sources & evidence

ORD record
ord-d0177a11fed84787bcfbdd7d6060ba62
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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