Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2364951Generated: October 26, 2026

Sodium Bicarbonate → 1-Butyl-3-chloro-4-[4-(4-oxo-cyclohexyl)-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl]-1H-pyridin-2-one

https://huagongshe.com/reaction/2364951

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium BicarbonateHCID 516892—
ReactantTrifluoromethanesulfonic acid 1-butyl-3-chloro-2-oxo-1,2-dihydropyridin-4-yl esterHCID 25221428—
ReactantHCID 178431016HCID 178431016—
CatalystHCID 178418397HCID 178418397—
Solvent1,4-DioxaneHCID 31275—
Product1-Butyl-3-chloro-4-[4-(4-oxo-cyclohexyl)-3,4-dihydro-2H-benzo[1,4]oxazin-7-yl]-1H-pyridin-2-oneHCID 5850531015.6%

Reaction Steps

A mixture of intermediate D15 (0.15 g, 0.418 mmol), intermediate D4 (0.139 g, 0.418 mmol), tetrakis(triphenylphosphine)palladium(0) (0.0241 g, 0.0209 mmol) and an aqueous saturated NaHCO3 solution (1 ml) in dioxane (4 ml), was heated at 150° C. for 10 min. under microwave irradiation. After cooling to r.t., the r.m. was filtered through diatomaceous earth, treated with EtOAc and the organic layer was washed with water and then with brine. The organic fraction was dried (Na2SO4), filtered and the solvent was evaporated in vacuo. The crude residue was purified by column chromatography (silica gel; 0-10% EtOAc/DCM as eluent). The desired fractions were collected and evaporated in vacuo to yield D23 (0.027 g, 15.59%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08697689B2
Source datasetuspto-grants-2014_04
ORD IDord-edda7789c415415287c15406eebff1f6
Source noteuspto-grants-2014_04