Cesium carbonate → HCID 67184530, compound

HRID 45828Notes

Reaction equation

HRID 45828 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].Cl[CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13].[N:16]1[CH:21]=[CH:20][C:19]([C:22]2[C:23]([C:27]3[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=3)[C:30]#[N:31])=[N:24][NH:25][CH:26]=2)=[CH:18][CH:17]=1>CN(C=O)C>[N:16]1[CH:17]=[CH:18][C:19]([C:22]2[C:23]([C:27]3[CH:28]=[C:29]([CH:32]=[CH:33][CH:34]=3)[C:30]#[N:31])=[N:24][N:25]([CH2:8][O:9][CH2:10][CH2:11][Si:12]([CH3:15])([CH3:14])[CH3:13])[CH:26]=2)=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether2×HCID 178509727HCID 178509727, compound

Product 1

HCID 67184530HCID 67184530, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (8.34 g, 25.6 mmol) and (2-chloromethoxy-ethyl)-trimethyl-silane (1.71 g, 10.24 mmol) were added to a solution of 3-(4-pyridin-4-yl-1H-pyrazol-3-yl)-benzonitrile (2.10 g, 8.54 mmol) in dry DMF (70 ml) and the reaction mixture was stirred at room temperature under nitrogen atmosphere for 24 h. A further addition of (2-chloromethoxy-ethyl)-trimethyl-silane (0.57 g, 3.41 mmol) was required to affect reaction completion; the solvent was then removed under reduced pressure and the residue was taken up with DCM (50 ml). The organic layer was washed with a saturated NaHCO3 solution (1×50 ml), brine (1×50 ml), dried over Na2SO4. The filtrate was evaporated to dryness to give a brown oil, which was purified by flash chromatography, over silica gel, using DCM/MeOH/NH4OH (9.8:0.2:0.1) as eluent, to afford 3-[4-pyridin-4-yl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrazol-3-yl]-benzonitrile (2.57 g, 6.82 mmol, 80%).

Workup

  1. customreaction completion
  2. customthe solvent was then removed under reduced pressure
  3. washThe organic layer was washed with a saturated NaHCO3 solution (1×50 ml), brine (1×50 ml)
  4. dry with materialdried over Na2SO4
  5. customThe filtrate was evaporated to dryness
  6. customto give a brown oil, which
  7. customwas purified by flash chromatography, over silica gel

Sources & evidence

ORD record
ord-ce768038dac242cc8024116f7d5e5612
Source dataset
uspto-grants-2013_09
Patent number
US08541575B2

Reaction notes

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