Dimethylformamide → HCID 57736547, compound

HRID 1641681Notes

Reaction equation

HRID 1641681 reaction equation
CCCCCC.C([Li])CCC.Br[C:13]1[CH:18]=[C:17]([CH3:19])[C:16]([CH:20]([C:29]2[CH:34]=[C:33]([F:35])[CH:32]=[CH:31][C:30]=2[F:36])[S:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)=[CH:15][N:14]=1.CN(C)[CH:39]=[O:40]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[F:36][C:30]1[CH:31]=[CH:32][C:33]([F:35])=[CH:34][C:29]=1[CH:20]([S:21][C:22]1[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=1)[C:16]1[C:17]([CH3:19])=[CH:18][C:13]([CH:39]=[O:40])=[N:14][CH:15]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 57736453HCID 57736453, compoundHCID 178418339Butyllithium

Product 1

HCID 57736547HCID 57736547, compoundYield 60%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In an argon atmosphere, a hexane solution of n-butyllithium M, 22.3 ml, 34.4 mmol) was added to a solution of 2-bromo-5-[(2,5-difluorophenyl)[(4-fluorophenyl)thio]methyl]-4-methylpyridine (8.10 g, 19.1 mmol) in toluene (200 ml) at −78° C. The reaction mixture was stirred for 30 minutes, and then N,N-dimethylformamide (1.63 ml, 21.0 mmol) was added at the same temperature. The reaction mixture was stirred for 30 minutes, then water was added 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 aqueous ammonium chloride, and then with saturated brine. 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 hexane:ethyl acetate=10:1 was concentrated under reduced pressure, and the resulting residue was washed with a mixed solvent of diethyl ether and hexane and then collected by filtration, thus to obtain the title compound (4.27 g, 11.4 mmol, 60%) as a white solid.

Workup

  1. stirringThe reaction mixture was stirred for 30 minutes
  2. washthe resulting mixture was washed with saturated aqueous ammonium chloride
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe fraction obtained from an elution with hexane
  7. concentrationethyl acetate=10:1 was concentrated under reduced pressure
  8. washthe resulting residue was washed with a mixed solvent of diethyl ether and hexane
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-d4ac3fce63454535a5a20e8335876350
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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