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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1472280Generated: October 30, 2026

Potassium Carbonate → 1-(4-t-Butoxycarbonyl-benzyl)-5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester

https://huagongshe.com/reaction/1472280

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
ReactantLithium ChlorideHCID 433294—
Reactantethyl 3-propyl-1H-pyrazole-5-carboxylateHCID 7365260—
ReactantTert-butyl 4-(bromomethyl)benzoateHCID 11414578—
SolventDimethylformamideHCID 6228—
Product1-(4-t-Butoxycarbonyl-benzyl)-5-propyl-1H-pyrazole-3-carboxylic acid ethyl esterHCID 59830914—

Reaction Steps

To the recovered intermediate (19a) (1.4 g, 5 mmol, 1.0 eq) dissolved into 15 mL DMF, was added 5-propyl-1H-pyrazole-3-carboxylic acid ethyl ester (910 mg, 5.0 mmol, 1.0 eq) and potassium carbonate (0.8 g, 5.5 mmol, 1.1 eq) and the mixture was stirred at room temperature for 16 hours. The mixture was then added to 50 mL of 10% aq. LiCl solution and extracted with 50 mL EtOAc. The organic was dried over MgSO4, and concentrated under reduced pressure to yield intermediate (19b) and its regioisomer in a 1:1 ratio. The recovered regioisomers were dissolved into 25 mL MeOH. To this was added 10 mL of 1M NaOH and the mixture was stirred at room temperature over night.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09012485B2
Source datasetuspto-grants-2015_04
ORD IDord-60e85cd7aeeb41c7bf14cea361b6bc05
Source noteuspto-grants-2015_04