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

HRID 1036노트

반응식

HRID 1036 반응식
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]

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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%.

후처리

  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)

출처 및 근거

ORD 기록
ord-8f013d8744a5498fbfa2b609c4f93dd7
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05723477

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