Dimethylformamide → Methyl 2-(4-formyl-3-methyl-pyrazol-1-yl)pyridine-3-carboxylate

HRID 1517569노트

반응식

HRID 1517569 반응식
[CH3:1][C:2]1[C:6]([CH:7]=[O:8])=[CH:5][NH:4][N:3]=1.C(=O)([O-])[O-].[K+].[K+].F[C:16]1[C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=1.CN(C)C=O>O>[CH:7]([C:6]1[C:2]([CH3:1])=[N:3][N:4]([C:16]2[C:21]([C:22]([O:24][CH3:25])=[O:23])=[CH:20][CH:19]=[CH:18][N:17]=2)[CH:5]=1)=[O:8]

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 242724Methyl 2-fluoronicotinateHCID 1784345503-methyl-1H-pyrazole-4-carbaldehyde

생성물 1

HCID 86653542Methyl 2-(4-formyl-3-methyl-pyrazol-1-yl)pyridine-3-carboxylate수율 63.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

A mixture of 3-methyl-1H-pyrazole-4-carbaldehyde (300 mg, 2.72 mmol), potassium carbonate (565 mg, 4.08 mmol), methyl 2-fluoropyridine-3-carboxylate (507 mg, 3.27 mmol) and dimethylformamide (2 mL) is stirred at 60° C. for 16 h. Water is added and the compound is extracted in ethyl acetate. The organic layer is washed with brine, dried over sodium sulfate and solvent is evaporated. The crude mixture is purified by normal phase Isco chromatography using hexane:ethyl acetate, 2:1 as eluent to yield 422 mg of the title compound. MS (m/z): 246 (M+1).

후처리

  1. extractionthe compound is extracted in ethyl acetate
  2. washThe organic layer is washed with brine
  3. dry with materialdried over sodium sulfate and solvent
  4. customis evaporated
  5. customThe crude mixture is purified by normal phase Isco chromatography

출처 및 근거

ORD 기록
ord-f549775b1fe94cf1b2f647957482649a
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232289B2

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