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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2390791Generated: October 25, 2026

Sodium Carbonate → 3-(3-Tert-butyl-4-difluoromethoxy-phenyl)-2-methoxy-pyridine

https://huagongshe.com/reaction/2390791

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant(2-Methoxypyridin-3-yl)boronic acidHCID 2762709—
Reactant4-Bromo-2-tert-butyl-difluoromethoxy-benzeneHCID 67286430—
CatalystHCID 178418397HCID 178418397—
SolventMethanolHCID 887—
SolventDichloromethaneHCID 6344—
Product3-(3-Tert-butyl-4-difluoromethoxy-phenyl)-2-methoxy-pyridineHCID 6707000758%

Reaction Conditions

Temperature115 °C

Reaction Steps

step 2—A sealed tube containing 20 (129 mg, 0.464 mmol), 2-methoxy-3-pyridine boronic acid (37, 108 mg, 0.706 mmol, CASRN 163105-90-6), Pd(PPh3)4 (39 mg, 0.034 mmol) and Na2CO3 (147 mg, 1.387 mmol) in a mixture of MeOH (3 mL) and DCM (1 mL) was heated in a microwave synthesizer at 115° C. for 30 min. The organic volatiles were removed under reduced pressure. The residue was partitioned between EtOAc and water. The organic layer was washed with brine, dried (Na2SO4), filtered and concentrated. The crude residue was purified by SiO2 chromatography eluting with a EtOAc/hexane gradient (0 to 5% EtOAc) to afford 82 mg (58%) of 3-(3-tert-butyl-4-difluoromethoxy-phenyl)-2-methoxy-pyridine (22) as an oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08273773B2
Source datasetuspto-grants-2012_09
ORD IDord-9193624c7cf446d3849efe39f7b72495
Source noteuspto-grants-2012_09