Water → HCID 57736518, compound

HRID 1641718Notes

Reaction equation

HRID 1641718 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]([C:19]2[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=2[F:26])[S:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[C:13]([CH3:18])[CH:12]=2)=[CH:4][N:3]=1.C([Li])CCC.CN(C)[CH:34]=[O:35].O>C1(C)C=CC=CC=1>[F:26][C:20]1[CH:21]=[CH:22][C:23]([F:25])=[CH:24][C:19]=1[CH:9]([S:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[C:13]([CH3:18])[CH:12]=1)[C:5]1[C:6]([CH3:8])=[CH:7][C:2]([CH:34]=[O:35])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 57736452HCID 57736452, compoundHCID 178418339Butyllithium

Product 1

HCID 57736518HCID 57736518, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of 2-bromo-5-[(2,5-difluorophenyl)[(4-fluoro-3-methylphenyl)thio]methyl]-4-methylpyridine (2.0 g, 4.6 mmol) in toluene (50 ml) was cooled to −78° C., and in an argon atmosphere, n-butyllithium (1.54 M hexane solution, 3.6 ml, 5.5 mmol) was added thereto. 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 then N,N-dimethylformamide (424 μl, 5.5 mmol) was added. After stirring for 30 minutes at the same temperature, water was added thereto, 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=95:5 was concentrated under reduced pressure to obtain the title compound (1.1 g, 2.8 mmol, 63%) as a colorless oily substance.

Workup

  1. stirringstirred for 30 minutes
  2. temperaturecooled again to −78° C.
  3. additionwas added
  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=95:5 was concentrated under reduced pressure

Sources & evidence

ORD record
ord-19a1f8c0c6244b08b95346fa1a414576
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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