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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 61912Generated: October 25, 2026

3-Bromo-4-chloropyridine → HCID 66835317, compound

https://huagongshe.com/reaction/61912

Reaction equation

Participants

RoleNameHCIDCharge
Reactant3-Bromo-4-chloropyridineHCID 817696—
Reactant2-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11269872—
Reactant7-Methoxy-1,1-dimethyl-3,4-dihydronaphthalen-2(1H)-oneHCID 13011007—
ReactantSodium t-butoxideHCID 23676156—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventTolueneHCID 1140—
SolventEthyl AcetateHCID 8857—
ProductHCID 66835317HCID 668353174%

Reaction Conditions

Temperature100 °C

Reaction Steps

To 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 2.5 g), 3-bromo-4-chloro-pyridine (2 g), sodium t-butoxide (3 g), Pd2dba3 (476 mg), and S-Phos (512 mg), toluene (20 ml) was added, and the mixture was stirred and heated at 100° C. overnight under nitrogen atmosphere. After cooling, the reaction mixture was diluted with ethyl acetate and filtered through Celite. The organic layer was washed with saturated aqueous solution of sodium bicarbonate and saturated brine. Thereafter, the organic layer was dried over sodium sulfate. The residues obtained after concentration under reduced pressure were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (112 mg, 4%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09440922B2
Source datasetuspto-grants-2016_09
ORD IDord-0582a6c2a42b43f8a3e683f3bc3d7248
Source noteuspto-grants-2016_09