Cesium carbonate → 3-[5-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-2-nitro-phenyl]-2-(tetrahydro-pyran-4-ylmethyl)-acrylonitrile

HRID 658062Notes

Reaction equation

HRID 658062 reaction equation
F[C:2]1[CH:3]=[CH:4][C:5]([N+:19]([O-:21])=[O:20])=[C:6]([CH:8]=[C:9]([CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:10]#[N:11])[CH:7]=1.[O:22]1[CH2:27][CH2:26][CH2:25][O:24][CH:23]1[C:28]1[CH:29]=[C:30]([SH:34])[CH:31]=[CH:32][CH:33]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.C(OCC)(=O)C>[O:22]1[CH2:27][CH2:26][CH2:25][O:24][CH:23]1[C:28]1[CH:29]=[C:30]([S:34][C:2]2[CH:3]=[CH:4][C:5]([N+:19]([O-:21])=[O:20])=[C:6]([CH:8]=[C:9]([CH2:12][CH:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)[C:10]#[N:11])[CH:7]=2)[CH:31]=[CH:32][CH:33]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 578640833-[1,3]Dioxan-2-yl-benzenethiolHCID 689786393-(5-Fluoro-2-nitro-phenyl)-2-(tetrahydro-pyran-4-ylmethyl)-acrylonitrile

Product 1

HCID 687376013-[5-(3-[1,3]Dioxan-2-yl-phenylsulfanyl)-2-nitro-phenyl]-2-(tetrahydro-pyran-4-ylmethyl)-acrylonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(5-Fluoro-2-nitro-phenyl)-2-(tetrahydro-pyran-4-ylmethyl)-acrylonitrile (1.2 g, 4.07 mmol) and 3-[1,3]dioxan-2-yl-benzenethiol (0.8 g, 4.07 mmol) were added to a mixture of Cs2CO3 (2.78 g, 8.56 mmol) in DMF (100 mL). The resulting mixture was stirred at room temperature overnight, then diluted with ethyl acetate and washed with H2O. The organic phase was separated, dried with MgSO4, and filtered. The solvent was removed to yield an oil, which was purified by silica column chromatography (40% EtOAc/heptane) to yield an oil.

Workup

  1. washwashed with H2O
  2. customThe organic phase was separated
  3. dry with materialdried with MgSO4
  4. filtrationfiltered
  5. customThe solvent was removed
  6. customto yield an oil, which
  7. customwas purified by silica column chromatography (40% EtOAc/heptane)
  8. customto yield an oil

Sources & evidence

ORD record
ord-0e7736d15a2a4212ac8062ae85e49530
Source dataset
uspto-grants-2011_12
Patent number
US08076358B2

Reaction notes

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