Toluene → HCID 22248449, compound

HRID 914846Notes

Reaction equation

HRID 914846 reaction equation
[F:1][C:2]1[S:3][CH:4]=[CH:5][C:6]=1[CH2:7][C:8]([C:10]1[CH:15]=[CH:14][N:13]=[CH:12][CH:11]=1)=[O:9].[C:16]1([CH3:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(Br)C1C=CC=CC=1>[CH2:22]([N:13]1[CH2:14][CH:15]=[C:10]([CH:8]([OH:9])[CH2:7][C:6]2[CH:5]=[CH:4][S:3][C:2]=2[F:1])[CH2:11][CH2:12]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 1140TolueneHCID 22248423HCID 22248423, compound

Product 1

HCID 22248449HCID 22248449, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 7498Benzyl BromideSolvent

Conditions

Temperature
100 °C

Procedure

After dissolving 304 mg of 2-(2-fluoro-3-thienyl)-1-(4-pyridyl)ethanone in 2 ml of toluene, 0.20 ml of benzyl bromide was added, the mixture was stirred at 100° C. for 8 hours and the precipitate was filtered out. The filtered substance was dissolved in 10 ml of methanol, 157 mg of sodium borohydride was added thereto in small portions at a time while cooling on ice, and the mixture was stirred for 1 hour. The reaction solution was distilled off under reduced pressure, water was added and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate) to obtain the title compound (384 mg, 88% yield).

Workup

  1. additionwas added
  2. filtrationthe precipitate was filtered out
  3. dissolutionThe filtered substance was dissolved in 10 ml of methanol
  4. addition157 mg of sodium borohydride was added
  5. temperaturein small portions at a time while cooling on ice
  6. stirringthe mixture was stirred for 1 hour
  7. distillationThe reaction solution was distilled off under reduced pressure, water
  8. additionwas added
  9. extractionextraction
  10. washThe organic layer was washed with water and saturated brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. distillationthe solvent was distilled off under reduced pressure
  13. customThe residue was purified by NH silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-5b8565b3d5984ae98c97757a09b29da6
Source dataset
uspto-grants-2007_09
Patent number
US07265108B2

Reaction notes

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