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

HRID 1517569ノート

反応式

HRID 1517569 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-f549775b1fe94cf1b2f647957482649a
出典データセット
uspto-grants-2012_07
特許番号
US08232289B2

反応ノート

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