Water → HCID 57736526, compound

HRID 1641714Notes

Reaction equation

HRID 1641714 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]([CH3:17])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.C([Li])CCC.CN(C)[CH:33]=[O:34].O>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]([CH3:17])=[CH:13][CH:12]=1)[C:5]1[C:6]([CH3:8])=[CH:7][C:2]([CH:33]=[O:34])=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6228DimethylformamideHCID 57736473HCID 57736473, compoundHCID 178418339Butyllithium

Product 1

HCID 57736526HCID 57736526, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-40 °C

Procedure

A solution of 2-bromo-5-[(2,5-difluorophenyl)[(4-methylphenyl)thio]methyl]-4-methylpyridine (2.5 g, 6.0 mmol) in toluene (60 ml) was cooled to −78° C., and in an argon atmosphere, n-butyllithium (1.54 M hexane solution, 4.6 ml, 7.1 mmol) was added thereto. After stirring for 10 minutes at the same temperature, the mixture was allowed to warm to −40° C. and stirred for 30 minutes. The mixture was cooled again to −78° C., and then N,N-dimethylformamide (720 μl, 7.1 mmol) was added. After stirring for 30 minutes at the same temperature, water was added, 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 (900 mg, 2.4 mmol, 41%) as a pale yellow oily substance.

Workup

  1. stirringstirred for 30 minutes
  2. temperatureThe mixture was cooled 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-6c807b99aa9e45e98ab9feef351d4efc
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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