Potassium Carbonate → 3-Methyl-1-(3-(tetrahydrofuran-2-yl)pyridin-2-yl)-1H-pyrazole-4-carbaldehyde

HRID 1517594ノート

反応式

HRID 1517594 の反応式
F[C:2]1[C:7]([CH:8]2[CH2:12][CH2:11][CH2:10][O:9]2)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH3:13][C:14]1[C:18]([CH:19]=[O:20])=[CH:17][NH:16][N:15]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[CH3:13][C:14]1[C:18]([CH:19]=[O:20])=[CH:17][N:16]([C:2]2[C:7]([CH:8]3[CH2:12][CH2:11][CH2:10][O:9]3)=[CH:6][CH:5]=[CH:4][N:3]=2)[N:15]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 671680662-Fluoro-3-(tetrahydrofuran-2-yl)pyridineHCID 1784345503-methyl-1H-pyrazole-4-carbaldehyde

生成物 1

HCID 582686413-Methyl-1-(3-(tetrahydrofuran-2-yl)pyridin-2-yl)-1H-pyrazole-4-carbaldehyde収率 60.9%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

反応条件

温度
110 °C

実験手順

To a screw-cap test tube containing 2-fluoro-3-(tetrahydrofuran-2-yl)pyridine (148 mg, 0.88 mmol) in dimethylformamide (2.2 mL) are added 3-methyl-1H-pyrazole-4-carbaldehyde (81 mg, 0.74 mmol) and potassium carbonate (152 mg, 1.1 mmol). The reaction tube is quickly sealed (caution: build-up of pressure possible; use a safety shield) and stirred in a preheated oil bath at 110° C. for 18 h with the aid of a magnetic stirrer. The mixture is diluted with water and extracted with ethyl acetate. The organic layer is separated, dried over magnesium sulfate, filtered and the solvent evaporated in vacuo. The resulting residue is purified by silica gel using normal phase Isco chromatography eluting with hexane: acetone (gradient from 5 to 20% in acetone) to give 116 mg of the title compound. MS (m/z): 258 (M+1).

後処理

  1. customThe reaction tube is quickly sealed (caution
  2. extractionextracted with ethyl acetate
  3. customThe organic layer is separated
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo
  7. customThe resulting residue is purified by silica gel using normal phase Isco chromatography
  8. washeluting with hexane

出典と根拠

ORDレコード
ord-dbde9c40725e4f1aad3eccee8b174161
出典データセット
uspto-grants-2012_07
特許番号
US08232289B2

反応ノート

読み込み中…