Triethylamine → 1-(3-Bromo-phenyl)-3,5-diethyl-1H-pyrazole-4-carboxylic acid methyl ester

HRID 1011863Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:14])[C:4]([C:10](=O)[CH2:11][CH3:12])=[C:5](OC)[CH2:6][CH3:7].Cl.[Br:16][C:17]1[CH:18]=[C:19]([NH:23][NH2:24])[CH:20]=[CH:21][CH:22]=1.CCN(CC)CC>CO>[CH3:1][O:2][C:3]([C:4]1[C:10]([CH2:11][CH3:12])=[N:24][N:23]([C:19]2[CH:20]=[CH:21][CH:22]=[C:17]([Br:16])[CH:18]=2)[C:5]=1[CH2:6][CH3:7])=[O:14]

Participants

Conditions

Temperature: -20 °C

Procedure

A solution of 7.10 g (35.5 mmol) of (E and/or Z)-3-methoxy-2-propionyl-pent-2-enoic acid methyl ester in 10 ml of MeOH was added to a solution of 8.09 g (35.5 mmol) of 3-bromophenylhydrazine hydrochloride in 150 ml of MeOH and the mixture was cooled to −20° C. To this mixture was added a solution of 3.79 g=5.22 ml (37.2 mmol) of Et3N in 40 ml of MeOH drop by drop and the reaction was then warmed up to RT. After 20 hours, it was poured into crashed ice and extracted twice with Et2O; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 7.62 g of the title compound as light red oil. MS: 337.1 (MH+, 1 Br).

Workup

temperaturethe reaction was then warmed up to RT
additionit was poured
extractionextracted twice with Et2O
washthe organic phases were washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-2ef6c5d1a79e480ea21fcd46cbeef319
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07977358B2

Reaction notes

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