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

HRID 215767

反応式

HRID 215767 の反応式
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

参加物

7

反応物 3

HCID 17307Ethyl 2-pyridinecarboxylateHCID 770224-IodopyrazoleHCID 178418339Butyllithium

生成物 1

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

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒HCID 8058Hexane溶媒HCID 25517Ammonium Chloride溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-10d50cd5288f4eca8dff9b9dfd123049
出典データセット
uspto-grants-2012_06
特許番号
US08193176B2

関連ノート

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