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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 886921Generated: October 28, 2026

Ethanol → HCID 68580291, compound

https://huagongshe.com/reaction/886921

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantSodium CarbonateHCID 10340—
Reactant3,5-Dimethylisoxazole-4-boronic acidHCID 2734346—
ReactantTert-butyl 9-bromo-2,3-dihydrobenzo[F][1,4]oxazepine-4(5H)-carboxylateHCID 59403519—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
ProductHCID 68580291HCID 6858029157.7%

Reaction Conditions

Temperature95 °C

Reaction Steps

A mixture of tert-butyl 9-bromo-2,3-dihydro-1,4-benzoxazepine-4(5H)-carboxylate (200 mg, 0.605 mmol), 3,5-dimethylisoxazol-4-ylboronic acid (129 mg, 0.912 mmol), ethanol (0.7 ml), 2N aqueous sodium carbonate solution (2.5 ml), and tetrakis(triphenylphosphine)palladium(0) (84.0 mg, 0.0730 mmol) in toluene (5 ml) was stirred under a nitrogen atmosphere at 95° C. for 12 hr. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=2:1) to give the desired product (120 mg, 57.7%) as an oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08247403B2
Source datasetuspto-grants-2012_08
ORD IDord-fcf5c6d545c64da3acb317d507809587
Source noteuspto-grants-2012_08