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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2275284Generated: October 31, 2026

2-Dicyclohexylphosphino-2',6'-dimethoxybiphenyl → 7-Methoxy-3-(3-methoxymethoxy-pyridin-4-yl)-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one

https://huagongshe.com/reaction/2275284

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 11269872—
Reactant4-Iodo-3-(methoxymethoxy)pyridineHCID 12955824—
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—
Product7-Methoxy-3-(3-methoxymethoxy-pyridin-4-yl)-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-oneHCID 6683516647.4%

Reaction Conditions

Temperature70 °C

Reaction Steps

To 7-methoxy-1,1-dimethyl-3,4-dihydro-1H-naphthalen-2-one (Compound A2, 924 mg), 4-iodo-3-methoxymethoxy-pyridine (1 g), sodium t-butoxide (906 mg), Pd2dba3 (173 mg) and S-Phos (185 mg), toluene (19 ml) was added, and the mixture was stirred and heated at 70° C. for 2 hrs under nitrogen atmosphere. 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, and then concentrated under reduced pressure. The resulting residues were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (610 mg, 47%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09126931B2
Source datasetuspto-grants-2015_09
ORD IDord-ae28e539bb964aaf8612b3fa52c539c3
Source noteuspto-grants-2015_09