Cesium carbonate → 3-Ethynyl-5-(1-methyl-2-pyrrolidinyl)pyridine

HRID 1489399Notes

Reaction equation

HRID 1489399 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[C:9]([CH:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH3:18])[CH:10]=[N:11][CH:12]=1)(C)C.C(=O)([O-])[O-].[Cs+].[Cs+]>CO>[C:6]([C:7]1[CH:8]=[C:9]([CH:13]2[CH2:17][CH2:16][CH2:15][N:14]2[CH3:18])[CH:10]=[N:11][CH:12]=1)#[CH:5]

Participants

4

Reactant 2

HCID 10796Cesium carbonateHCID 196942995-Trimethylsilylethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine

Product 1

HCID 1331063-Ethynyl-5-(1-methyl-2-pyrrolidinyl)pyridine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Repeating the procedure of Example 16, but using trimethylsilylacetylene in place of phenylacetylene, 5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine and the fumarate derivative thereof were obtained as follows. 5-Trimethylsilylethynyl-3-(1-methyl-2-pyrrolidinyl) pyridine (516 mg, 2 mmol) and cesium carbonate (200 mg, 0.6 mmol) were dissolved in methanol (10 mL) and heated under reflux for 5 h. After cooling the solvents were removed in vacuo and the residue dissolved in ethyl acetate (40 mL) and washed with water (10 mL). The aqueous layer was extracted with ethyl acetate (40 mL) and the combined organic extracts washed with brine (10 mL), dried (Na2SO4) and concentrated in vacuo. The crude product was chromatographed on "flash" silica gel with ethyl acetate:hexane (1:9, 1:4, 1,3) to afford 5-ethynyl-3-(1-methyl-2-pyrrolidinyl)pyridine as an oil, 218 mg, 59%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 5 h
  3. temperatureAfter cooling the solvents
  4. customwere removed in vacuo
  5. dissolutionthe residue dissolved in ethyl acetate (40 mL)
  6. washwashed with water (10 mL)
  7. extractionThe aqueous layer was extracted with ethyl acetate (40 mL)
  8. washthe combined organic extracts washed with brine (10 mL)
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated in vacuo
  11. customThe crude product was chromatographed on "flash" silica gel with ethyl acetate:hexane (1:9, 1:4, 1,3)

Sources & evidence

ORD record
ord-3beaf837db6e49048e6311dc7278ef48
Source dataset
uspto-grants-1997_10
Patent number
US05677459

Reaction notes

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