Potassium Carbonate → Ethyl 3-amino-1-[(4-methoxyphenyl)methyl]-1H-pyrazole-4-carboxylate

HRID 1520229Notes

Reaction equation

Cl[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=1.C([O-])([O-])=O.[K+].[K+].[NH2:17][C:18]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][NH:20][N:19]=1>C(#N)C>[NH2:17][C:18]1[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:21][N:20]([CH2:2][C:3]2[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][CH:4]=2)[N:19]=1

Participants

Conditions

Temperature: 60 °C

Procedure

According to Scheme 15 Step 1: 1-(Chloromethyl)-4-methoxybenzene (12.9 mmol, 2.02 g) followed by K2CO3 (25.8 mmol, 3.56 g) were added to a solution of ethyl 3-amino-1H-pyrazole-4-carboxylate (12.9 mmol, 2.00 g) in acetonitrile (10 mL) and then the reaction mixture was heated at 60° C. for 3 hours. After evaporation of the solvent, a saturated solution of Na2CO3 was added and the aqueous phase was extracted with AcOEt. The organic phase was dried over Na2SO4, was filtered and was concentrated under reduced pressure. The crude product was purified by flash chromatography over silica gel using cyclohexane/AcOEt (100:0 to 20:80) as eluent to afford ethyl 3-amino-1-(4-methoxybenzyl)-1H-pyrazole-4-carboxylate (6.90 mmol, 1.90 g, 53%) as a white powder.

Workup

customAfter evaporation of the solvent
additiona saturated solution of Na2CO3 was added
extractionthe aqueous phase was extracted with AcOEt
dry with materialThe organic phase was dried over Na2SO4
filtrationwas filtered
concentrationwas concentrated under reduced pressure
customThe crude product was purified by flash chromatography over silica gel

Sources & evidence

ORD record: ord-d6607c247c9a4a488266fa31d3990d3a
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09073907B2

Reaction notes

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