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

HRID 1517594노트

반응식

HRID 1517594 반응식
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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

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온도
110 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dbde9c40725e4f1aad3eccee8b174161
출처 데이터셋
uspto-grants-2012_07
특허 번호
US08232289B2

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