Dimethylformamide → HCID 57736519, compound

HRID 1641743Notes

Reaction equation

HRID 1641743 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=2[F:18])=[CH:4][N:3]=1.CCCCCC.C([Li])CCC.CN(C)[CH:39]=[O:40]>C1(C)C=CC=CC=1.C(OCC)(=O)C.O>[CH3:8][C:6]1[C:5]([CH:9]([S:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[C:10]2[C:15]([F:16])=[CH:14][CH:13]=[C:12]([F:17])[C:11]=2[F:18])=[CH:4][N:3]=[C:2]([CH:39]=[O:40])[CH:7]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 8058HexaneHCID 57736546HCID 57736546, compoundHCID 178418339Butyllithium

Product 1

HCID 57736519HCID 57736519, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 2-bromo-4-methyl-5-[(phenylthio)(2,3,6-trifluorophenyl)meth yl]pyridine (2.00 g, 4.40 mmol) in toluene (40 ml), a hexane solution of n-butyllithium (1.58 M, 3.3 ml, 5.28 mmol) was added in an argon atmosphere at −75° C. The reaction mixture was stirred for 1 hour at −40° C., and then cooled again to −75° C., and N,N-dimethylformamide (0.68 ml, 8.80 mmol) was added. After Completion of dropwise addition, the reaction mixture was allowed to warm to 0° C., and water was added to the same temperature. Ethyl acetate was added to the reaction mixture, the organic layer was separated, and then the organic layer was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting residue was subjected to flash silica gel chromatography. The fraction obtained from an elution with hexane:ethyl acetate was concentrated under reduced pressure to obtain the title compound (1.03 g, 2.76 mmol, 63%) as a pale yellow oily substance.

Workup

  1. temperaturecooled again to −75° C.
  2. additionAfter Completion of dropwise addition
  3. temperatureto warm to 0° C.
  4. customthe organic layer was separated
  5. washthe organic layer was washed with saturated brine
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe fraction obtained from an elution with hexane
  10. concentrationethyl acetate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-94a3703365814e96ad018750fac138d0
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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