Dimethylformamide → HCID 23114603, compound

HRID 2080492Notes

Reaction equation

HRID 2080492 reaction equation
C([Li])CCC.Br[C:7]1[CH:12]=[C:11]([CH:13]([S:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])[C:10]([Br:30])=[CH:9][N:8]=1.CN(C)[CH:33]=[O:34].[BH4-].[Na+]>CCCCCC.O.CO.C1(C)C=CC=CC=1>[Br:30][C:10]1[C:11]([CH:13]([S:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[C:14]2[CH:19]=[C:18]([F:20])[CH:17]=[CH:16][C:15]=2[F:21])=[CH:12][C:7]([CH2:33][OH:34])=[N:8][CH:9]=1

Participants

9

Reactant 4

HCID 6228DimethylformamideHCID 4311764Sodium borohydrideHCID 23114850HCID 23114850, compoundHCID 178418339Butyllithium

Product 1

HCID 23114603HCID 23114603, compoundYield 89%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 1140TolueneSolventHCID 8058HexaneSolvent2×

Procedure

Under an argon atmosphere, n-butyl lithium (a 1.59M hexane solution, 0.27 ml, 0.435 mmol) was added to a toluene (10 ml) solution of 2,5-dibromo-4-[(4-chlorophenylthio)(2,5-difluorophenyl)methyl]pyridine (200 mg, 0.396 mmol) at −78° C. The reaction mixture was stirred for 2 hours. To the reaction mixture was added dropwise dimethylformamide (40 μl, 0.514 mmol), followed by stirring for 1 hour. To the reaction mixture were added methanol (10 ml) and sodium borohydride (30 mg, 0.791 mmol). The temperature of the resulting mixture was raised to room temperature. The reaction mixture was stirred for 1 hour. After addition of water, the resulting mixture was extracted with ethyl acetate. The extract was washed with brine. The organic layer thus obtained was dried over magnesium sulfate, and concentrated under reduced pressure. The residue thus obtained was subjected to flash silica gel column chromatography. The fraction obtained from the hexane:ethyl acetate=3:1 eluate was concentrated under reduced pressure to give the title compound (160 mg, 0.350 mmol, 89%) as a colorless amorphous substance.

Workup

  1. stirringby stirring for 1 hour
  2. stirringThe reaction mixture was stirred for 1 hour
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with brine
  5. customThe organic layer thus obtained
  6. dry with materialwas dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue thus obtained
  9. concentrationethyl acetate=3:1 eluate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-8d52abebda2c44e5ab2aa34d66cc1489
Source dataset
uspto-grants-2011_04
Patent number
US07932271B2

Reaction notes

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