Dimethylformamide → HCID 57736506, compound

HRID 1641704Notes

Reaction equation

HRID 1641704 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]([O:17][CH3:18])=[CH:13][CH:12]=2)=[CH:4][N:3]=1.CCCCCC.C([Li])CCC.CN(C)[CH:40]=[O:41]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[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]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:5]1[C:6]([CH3:8])=[CH:7][C:2]([CH:40]=[O:41])=[N:3][CH:4]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 57736485HCID 57736485, compoundHCID 178418339Butyllithium

Product 1

HCID 57736506HCID 57736506, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 2-bromo-5-[(2,5-difluorophenyl)[(4-methoxyphenyl)thio]methyl]-4-methylpyridine (1.08 g, 2.48 mmol) in toluene (30 ml), a hexane solution of n-butyllithium (1.54 M, 1.77 ml, 2.72 mmol) was added in an argon atmosphere at −78° C. The reaction mixture was stirred for 30 minutes at −40° C., and then cooled again to −78° C., and N,N-dimethylformamide (0.221 ml, 2.72 mmol) was added thereto. After stirring the reaction mixture for 2 hours, water was added thereto at the same temperature, and the mixture was allowed to warm to room temperature. Ethyl acetate was added to the reaction mixture, and the resulting mixture was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate and filtered, then the filtrate was concentrated under reduced pressure, and the obtained residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate=10:1 was concentrated under reduced pressure to obtain the title compound (597 mg, 1.55 mmol, 63%) as a yellow oily substance.

Workup

  1. temperaturecooled again to −78° C.
  2. stirringAfter stirring the reaction mixture for 2 hours
  3. temperatureto warm to room temperature
  4. washthe resulting mixture was washed with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationthe filtrate was concentrated under reduced pressure
  8. customThe fraction obtained from an elution with hexane
  9. concentrationethyl acetate=10:1 was concentrated under reduced pressure

Sources & evidence

ORD record
ord-433cfa5f0b6945698c824bb294b825d6
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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