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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 920608Generated: October 28, 2026

Ethyl Acetate → HCID 54766120, compound

https://huagongshe.com/reaction/920608

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantSodium hydrideHCID 24758—
Reactant4-Amino-3,5-dichloropyridineHCID 89888—
ReactantHCID 67125498HCID 67125498—
SolventPentaneHCID 8003—
SolventTetrahydrofuranHCID 8028—
ProductHCID 54766120HCID 54766120—

Reaction Steps

4-Nitrophenyl 7-difluoromethoxy-2′,3′,5′,6′-tetrahydro-spiro[1,3-benzodioxole-2,4′-(4H)-thiopyran]-4-carboxylate (250 mg) and 3,5-Dichloro-4-aminopyridine (129 mg) was dissolved under argon in dry THF, 5 mL. Sodium hydride (50% suspension in oil), 40 mg, was added, and the mixture left stirring overnight. Aqueous work up with EtOAc and chromatography in a gradient from 0 to 60% EtOAc in pentane afforded the title compound. 1H NMR (300 MHz, CDCl3) δ 8.64 (s, 1H), 8.57 (s, 2H), 7.63 (d, J=9.0 Hz, 1H), 6.86 (d, J=9.1 Hz, 1H), 6.73 (t, J=72 Hz, 1H), 3.03-2.81 (m, 4H), 2.49-2.29 (m, 4H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09273064B2
Source datasetuspto-grants-2016_03
ORD IDord-85fb439597b248088339c412ad0b1f0c
Source noteuspto-grants-2016_03