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
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Sodium Sulfate | HCID 24436 | — |
| Reactant | 1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 2773987 | — |
| Reactant | 5-Bromo-4-fluoropyridin-2-amine | HCID 57917407 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | 4-fluoro-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine | HCID 118046326 | 75.4% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09242996B2 |
|---|
| Source dataset | uspto-grants-2016_01 |
|---|
| ORD ID | ord-87b5327baa2849cdb19181ed34b9d597 |
|---|
| Source note | uspto-grants-2016_01 |
|---|