Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 57873Generated: October 25, 2026

Sodium Carbonate → Tert-butyl 4-[6-[6-(2-fluoro-5-methyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-1,4-diazepane-1-carboxylate

https://huagongshe.com/reaction/57873

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantPotassium AcetateHCID 517044—
Reactant2-Fluoro-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 44717654—
ReactantTert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)pyrazin-2-yl]-1,4-diazepane-1-carboxylateHCID 86707066—
CatalystHCID 178418807HCID 178418807—
SolventAcetonitrileHCID 6342—
ProductTert-butyl 4-[6-[6-(2-fluoro-5-methyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-1,4-diazepane-1-carboxylateHCID 8670706984%

Reaction Conditions

Temperature150 °C

Reaction Steps

A mixture of tert-butyl 4-[6-(6-chloropyrazolo[4,3-c]pyridin-1-yl)pyrazin-2-yl]-1,4-diazepane-1-carboxylate (0.2526 mmol; 108.6 mg), 2-fluoro-5-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (0.3789 mmol; 89.84 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (0.02526 mmol; 21.1 mg), potassium acetate (0.3789 mmol; 0.38 mL) and sodium carbonate (0.3789 mmol; 0.38 mL) in Acetonitrile (10 mL) in a pressure tube was heated under microwave at 150° C. for 15 min. The mixture was cooled to room temperature. The layers were separated. The aqueous layer was extracted with EtOAc. The combined organic layers were concentrated. The residue was purified on silica eluted with 0 to 5% MeOH in DCM with 1% NH4OH to afford tert-butyl 4-[6-[6-(2-fluoro-5-methyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]pyrazin-2-yl]-1,4-diazepane-1-carboxylate (106.6 mg, 84%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09434725B2
Source datasetuspto-grants-2016_09
ORD IDord-05bc36ceca694d228428b105492fc604
Source noteuspto-grants-2016_09