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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2207423Generated: November 1, 2026

Sodium Carbonate → HCID 131735917, compound

https://huagongshe.com/reaction/2207423

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant5-Bromopyridine-2-carbaldehydeHCID 9877562—
ReactantN-(3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-4-(trifluoromethyl)pyrimidin-2-amineHCID 58456089—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
Solvent1,4-DioxaneHCID 31275—
ProductHCID 131735917HCID 131735917—

Reaction Steps

A mixture of 5-bromopyridine-2-carbaldehyde (500 mg, 2.69 mmol), N-[3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]-4-(trifluoromethyl)pyrimidin-2-amine (1.23 g, 3.24 mmol), PdCl2(dppf) (216 mg, 0.295 mmol), sodium carbonate (2 M, 2.70 mL, 5.40 mmol), and dioxane (10.0 mL) was evacuated and purged with Ar(g) (3×), and then irradiated under microwave at 100° C. for 10 minutes. The mixture was filtered, diluted with ethyl acetate and washed with water. The organic layer was concentrated under reduced pressure and the residue was purified by silica gel chromatography (25% ethyl acetate in hexanes) to afford 5-(3-methyl-5-{[4-(trifluoromethyl)pyrimidin-2-yl]amino}phenyl)pyridine-2-carbaldehyde. C18H14F3N4O [M+H]+ 359. found 359.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09376418B2
Source datasetuspto-grants-2016_06
ORD IDord-f6deffd9d1c7485fbd1d097558eef0c4
Source noteuspto-grants-2016_06