Ethyl 2-pyridinecarboxylate → (1H-pyrazol-4-yl)-pyridin-2-ylmethanone

HRID 215767

반응식

HRID 215767 반응식
I[C:2]1[CH:3]=[N:4][NH:5][CH:6]=1.C([Li])CCC.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[C:18](OCC)=[O:19]>O1CCCC1.CCCCCC.[Cl-].[NH4+]>[NH:4]1[CH:3]=[C:2]([C:18]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=2)=[O:19])[CH:6]=[N:5]1

참가 물질

7

반응물 3

HCID 17307Ethyl 2-pyridinecarboxylateHCID 770224-IodopyrazoleHCID 178418339Butyllithium

생성물 1

HCID 15163295(1H-pyrazol-4-yl)-pyridin-2-ylmethanone수율 10.1%

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매HCID 25517Ammonium Chloride용매

실험 절차

To a solution of 4-iodopyrazole (1.0 g) in tetrahydrofuran (10 mL), a solution of n-butyllithium in hexane (2.6 M, 4.8 mL) was added dropwise at −10° C. and stirred at room temperature for 1 hour. The reaction mixture was cooled to −10° C. and ethyl picolinate (0.86 g) was added thereto, followed by stirring at room temperature for 1.5 hours. The reaction mixture was diluted with saturated aqueous ammonium chloride and extracted with diethyl ether. The organic layer was washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: hexane:ethyl acetate=1:1 to 1:2) to give the titled compound (0.090 g) as a colorless solid.

후처리

  1. temperatureThe reaction mixture was cooled to −10° C.
  2. stirringby stirring at room temperature for 1.5 hours
  3. extractionextracted with diethyl ether
  4. washThe organic layer was washed with brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was purified by NH-type silica gel column chromatography (eluting solvent: hexane:ethyl acetate=1:1 to 1:2)

출처 및 근거

ORD 기록
ord-10d50cd5288f4eca8dff9b9dfd123049
출처 데이터셋
uspto-grants-2012_06
특허 번호
US08193176B2

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