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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 905905Generated: October 30, 2026

Hydrochloric Acid → HCID 59340101, compound

https://huagongshe.com/reaction/905905

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
ReactantSodium CarbonateHCID 10340—
Reactant3,5-Dimethylisoxazole-4-boronic acidHCID 2734346—
ReactantMethyl 2-(7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetateHCID 54681697—
CatalystHCID 178418397HCID 178418397—
SolventChloroformHCID 6212—
SolventDimethylformamideHCID 6228—
Solvent1,2-DimethoxyethaneHCID 8071—
ProductHCID 59340101HCID 59340101—

Reaction Conditions

Temperature75 °C

Reaction Steps

A mixture of methyl 2-(7-bromo-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxamido)acetate (400 mg, 1084 μmol), 3,5-dimethylisoxazol-4-ylboronic acid (305 mg, 2167 μmol) and Pd(PPh3)4 (125 mg, 108 μmol) in 8 ml 1,2-dimethoxyethane (or DMF) and 1.6 ml 2M aqueous Na2CO3 was heated to 75° C. and stirred for 12 hours. The mixture was cooled to 24° C., treated with 1M aqueous HCl and CHCl3, after which solids precipitated. The organic layer was separated and the solids were collected by filtration, and washed with MeOH.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08012968B2
Source datasetuspto-grants-2011_09
ORD IDord-82a42480bc95417499d5f1cc4bfcd055
Source noteuspto-grants-2011_09