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

HRID 1517594Notes

Reaction equation

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

Participants

Conditions

Temperature: 110 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-dbde9c40725e4f1aad3eccee8b174161
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232289B2

Reaction notes

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