Dimethylformamide → HCID 57736495, compound

HRID 1641752Notes

Reaction equation

HRID 1641752 reaction equation
Br[C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]([S:19][C:20]2[CH:21]=[N:22][C:23]([C:26]([F:29])([F:28])[F:27])=[CH:24][CH:25]=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.C([Li])CCC.CN(C)[CH:37]=[O:38].[Cl-].[NH4+]>C1(C)C=CC=CC=1.O.ClCCl.CCCCCC>[CH3:8][C:6]1[C:5]([CH:9]([S:19][C:20]2[CH:21]=[N:22][C:23]([C:26]([F:27])([F:29])[F:28])=[CH:24][CH:25]=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:37]=[O:38])[CH:7]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 57736489HCID 57736489, compoundHCID 178418339Butyllithium

Product 1

HCID 57736495HCID 57736495, compoundYield 59.1%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 1140TolueneSolventHCID 6344DichloromethaneSolventHCID 8058HexaneSolvent

Conditions

Temperature
-40 °C

Procedure

To a solution of 2-bromo-4-methyl-5-[[[6-(trifluoromethyl)pyridin-3-yl]thio](2,3,6-trifluorophenyl)methyl]pyridine (4.76 g, 9.65 mmol) in toluene (100 ml), a hexane solution of n-butyllithium (1.58 M, 6.72 ml, 10.6 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 (0.897 ml, 11.6 mmol) was added. After completion of dropwise addition, the reaction mixture was allowed to warm to 0° C., and saturated aqueous ammonium chloride was added thereto at the same temperature. Dichloromethane and water were added to the reaction mixture, and the organic layer was separated. Subsequently, the organic layer was 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 chromatography, and the fraction obtained from an elution with hexane:ethyl acetate=5:1 was concentrated under reduced pressure, to obtain the title compound (2.52 g, 5.70 mmol, 59%) as a yellow oily substance.

Workup

  1. temperaturecooled again to −78° C.
  2. additionAfter completion of dropwise addition
  3. temperatureto warm to 0° C.
  4. customthe organic layer was separated
  5. dry with materialSubsequently, the 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=5:1 was concentrated under reduced pressure

Sources & evidence

ORD record
ord-68d839063b11489997f3206ddff0eeaa
Source dataset
uspto-grants-2012_02
Patent number
US08114886B2

Reaction notes

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