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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1405900Generated: November 2, 2026

Pyridine → (9S)-9-[4-(4-chloro-2-methylphenoxy)phenyl]-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxide

https://huagongshe.com/reaction/1405900

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPyridineHCID 1049—
ReactantCesium carbonateHCID 10796—
Reactant(4-Chloro-2-methylphenyl)boronic acidHCID 5017600—
Reactant4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenolHCID 66748496—
CatalystHCID 178476681HCID 178476681—
SolventAcetonitrileHCID 6342—
Product(9S)-9-[4-(4-chloro-2-methylphenoxy)phenyl]-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazine 2,2-dioxideHCID 667487725.1%

Reaction Steps

A mixture of (4-chloro-2-methylphenyl)boronic acid (912 mg), 4-[(9S)-2,2-dioxido-3,4,6,7,8,9-hexahydropyrido[2,1-c][1,2,4]thiadiazin-9-yl]phenol (500 mg), pyridine (3.60 mL), cesium carbonate (581 mg), diacetoxycopper (648 mg) and powdered 4A MS (5.00 g) in MeCN (18 mL) was stirred at room temperature overnight. The mixture was added with NH silica gel, concentrated in vacuo, and purified by column chromatography (NH silica gel, eluted with MeOH in EtOAc) to give the title compound (37.0 mg) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08916551B2
Source datasetuspto-grants-2014_12
ORD IDord-c1f9d8c16a8c42229615d73e931cacee
Source noteuspto-grants-2014_12