Benzyl mercaptan → HCID 22054776, compound

HRID 1526647Notes

Reaction equation

HRID 1526647 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:7][C:8]1[CH:9]=[CH:10][C:11](F)=[N:12][CH:13]=1.[CH2:15]([SH:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>CN(C=O)C.CCOCC>[CH2:15]([S:22][C:11]1[CH:10]=[CH:9][C:8]([Cl:7])=[CH:13][N:12]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 7509Benzyl mercaptanHCID 10796Cesium carbonateHCID 3458175-Chloro-2-fluoropyridine

Product 1

HCID 22054776HCID 22054776, compoundYield 101%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of cesium carbonate (3.76 g, 11.5 mmol) in DMF (20 mL) at room temperature was added 5-chloro-2-fluoropyridine (1.00 mL, 9.96 mmol) and benzylmercaptan (1.15 mL, 9.80 mmol). The reaction mixture was stirred at room temperature for 16 h and heated to 60° C. for 6 h. The reaction mixture was diluted with Et2O. The organic phase was washed with water (2×), brine and dried over MgSO4. The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography on silica gel (5% to 10% EtOAc in heptane) to give the title compound (2.33 g, 9.88 mmol, 101% yield) as a colorless oil that was used without further purification in the next step. MS) m/z=236.1 [M+H]+. Calculated for C12H10ClNS 235.0.

Workup

  1. temperatureheated to 60° C. for 6 h
  2. washThe organic phase was washed with water (2×), brine
  3. dry with materialdried over MgSO4
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by flash column chromatography on silica gel (5% to 10% EtOAc in heptane)

Sources & evidence

ORD record
ord-0b0261d4dfb642579f8b0bd72e1a494a
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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