Morpholine → 3-Methyl-1-(3-morpholino-2-pyridyl)pyrazole-4-carbaldehyde

HRID 1517578Notes

Reaction equation

F[C:2]1[C:3]([N:8]2[CH:12]=[C:11]([CH:13]=[O:14])[C:10]([CH3:15])=[N:9]2)=[N:4][CH:5]=[CH:6][CH:7]=1.[NH:16]1[CH2:21][CH2:20][O:19][CH2:18][CH2:17]1>ClCCl>[CH3:15][C:10]1[C:11]([CH:13]=[O:14])=[CH:12][N:8]([C:3]2[C:2]([N:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)=[CH:7][CH:6]=[CH:5][N:4]=2)[N:9]=1

Participants

Conditions

Temperature: 160 °C

Procedure

A mixture of 1-(3-fluoro-2-pyridyl)-3-methyl-pyrazole-4-carbaldehyde (230 mg, 1.12 mmol) and morpholine (2 mL, 22.93 mmol) is heated under microwave irradiation (temperature 160° C., ramp time: 2 min, hold time: 10 min, potency: 250 W). The excess of morpholine is eliminated in vacuo and the residue is diluted in dichloromethane and washed in saturated aqueous solution of sodium bicarbonate. The organic layer is separated, dried over magnesium sulfate and the solvent evaporated in vacuo. The residue is purified by normal phase Isco chromatography using hexane/ethyl acetate as eluent (from 50 to 100% in ethyl acetate) to yield 72% of the title compound. MS (m/z): 273 (M+1).

Workup

washwashed in saturated aqueous solution of sodium bicarbonate
customThe organic layer is separated
dry with materialdried over magnesium sulfate
customthe solvent evaporated in vacuo
customThe residue is purified by normal phase Isco chromatography

Sources & evidence

ORD record: ord-e307915f2955461581b92132a96adc3d
Source dataset: uspto-grants-2012_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08232289B2

Reaction notes

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