Ethanethiol → HCID 86618225, compound

HRID 1673267Notes

Reaction equation

HRID 1673267 reaction equation
[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]([C:23]1([C:26]([F:29])([F:28])[F:27])CO1)[CH2:11][NH:12][C:13]1[CH:22]=[CH:21][CH:20]=[C:19]2[C:14]=1[CH:15]=[CH:16]C=[N:18]2.[C:30](=[O:33])([O-])[O-].[Cs+].[Cs+].C(S)C>CN(C=O)C>[F:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[CH:10]([C:11]1[CH:16]=[CH:15][C:14]2[C:19]([NH2:18])=[CH:20][CH:21]=[CH:22][C:13]=2[N:12]=1)[C:23]1([C:26]([F:29])([F:28])[F:27])[CH2:30][O:33]1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 10796Cesium carbonateHCID 86618226HCID 86618226, compound

Product 1

HCID 86618225HCID 86618225, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

[(2-Fluoro-3-methoxyphenyl)-2-(2-trifluoromethyl-oxiranyl)ethyl]quinolin-5-yl-amine (97 mg, 0.25 mmol) was dissolved in DMF (0.5 mL). Caesium carbonate (161 mg, 0.5 mmol) was added followed by ethanethiol (75 μL, 1 mmol). The mixture was vigorously stirred at ambient temperature for 90 minutes. The reaction mixture was partitioned between diethylether and water. The organic phase was washed trice with water and then with brine and evaporated. The residue was dissolved in methylene chloride, filtered through a plug of glass wool to remove residual NaCl and again evaporated. The crude product was dissolved in methylene chloride and flash-chromatographed on a column of silica using a gradient of heptane-ethyl acetate (10→90% ethyl acetate) to yield the title product (60 mg, 53%) as an amorphous solid.

Workup

  1. customThe reaction mixture was partitioned between diethylether and water
  2. washThe organic phase was washed trice with water
  3. customwith brine and evaporated
  4. dissolutionThe residue was dissolved in methylene chloride
  5. filtrationfiltered through a plug of glass wool
  6. customto remove residual NaCl
  7. customagain evaporated
  8. dissolutionThe crude product was dissolved in methylene chloride
  9. customflash-chromatographed on a column of silica using a gradient of heptane-ethyl acetate (10→90% ethyl acetate)

Sources & evidence

ORD record
ord-742bb337c33540a4a6b3f4fd1bf5a5ac
Source dataset
uspto-grants-2011_08
Patent number
US07999108B2

Reaction notes

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