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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1480865Generated: November 1, 2026

Pivalic acid → HCID 89995597, compound

https://huagongshe.com/reaction/1480865

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPivalic acidHCID 6417—
ReactantPotassium CarbonateHCID 11430—
Reactant1,2-DimethylimidazoleHCID 15617—
Reactant6-Bromo-2-methoxypyridin-3-amineHCID 10536137—
ReactantTri(cyclohexyl)phosphine tetrafluoroborateHCID 20066521—
Catalystpalladium(II) acetateHCID 167845—
SolventEthyl AcetateHCID 8857—
SolventDimethylacetamideHCID 31374—
ProductHCID 89995597HCID 8999559735%

Reaction Conditions

Temperature120 °C

Reaction Steps

Palladium acetate (5.5 mg, 0.025 mmol) was added to a solution of 6-bromo-2-methoxypyridin-3-amine (25 mg, 0.123 mmol), 1,2-dimethyl-1H-imidazole (35.5 mg, 0.369 mmol), pivalic acid (3.8 mg, 0.037 mmol), tricyclohexylphosphine tetrafluoroborate salt (18.1 mg, 0.049 mmol) and potassium carbonate (25.5 mg, 0.185 mmol) in DMA (410 μL). The reaction mixture was heated under microwave irradiation at 120° C. for 1 hour. The reaction was diluted with EtOAc and quenched with water. The layers were separated and the aqueous layer was extracted with EtOAc. The combined organic layers were dried (Na2SO4), filtered and concentrated in vacuo. The crude mixture was purified by Biotage silica gel column chromatography eluting with 1 to 5% MeOH/aq. NH3 (10/1) in DCM to afford the title compound as a white solid (9 mg, 35%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09409907B2
Source datasetuspto-grants-2016_08
ORD IDord-a5794beed83143719ab4496183baf3f3
Source noteuspto-grants-2016_08