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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 595850Generated: October 30, 2026

Sodium Carbonate → 4-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine

https://huagongshe.com/reaction/595850

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantSodium SulfateHCID 24436—
Reactant1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 2773987—
Reactant5-Bromo-4-fluoropyridin-2-amineHCID 57917407—
Solvent1,2-DimethoxyethaneHCID 8071—
Product4-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amineHCID 11804632675.4%

Reaction Conditions

Temperature120 °C

Reaction Steps

To the reaction mixture of 5-bromo-4-fluoropyridin-2-amine (369 mg, 1.932 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (603 mg, 2.90 mmol), PdCl2(dppf)DCM (141 mg, 0.193 mmol) and DME (9.660 μL), 2M Na2CO3 (3.220 mL) was added. The reaction mixture was heated at microwave synthesizer (120° C., 12 min). To the reaction mixture, anhydrous sodium sulfate was added, filtered, and concentrated. The crude product was purified by flash chromatography eluting with 0-100% EtOAc (containing 10% of MeOH/heptane to provide 280 mg of desired product in 75% yield. LCMS (m/z): 193.1 (MH+), 0.35 min.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09242996B2
Source datasetuspto-grants-2016_01
ORD IDord-87b5327baa2849cdb19181ed34b9d597
Source noteuspto-grants-2016_01