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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 278686Generated: October 29, 2026

Tetrahydrofuran → 4-[(8-Cyclopropyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl ester

https://huagongshe.com/reaction/278686

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTetrahydrofuranHCID 8028—
ReactantTriethylamineHCID 8471—
ReactantMethyl 2-fluoro-4-iodobenzoateHCID 22568800—
Reactant8-Cyclopropyl-6-ethynyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cvclopropane]HCID 22568951—
CatalystHCID 178418476HCID 178418476—
SolventHexaneHCID 8058—
SolventEthyl AcetateHCID 8857—
Product4-[(8-Cyclopropyl-3 4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1'-cyclopropane]-6-yl)ethynyl]-2-fluoro-benzoic acid methyl esterHCID 69548418—

Reaction Steps

Following general procedure F and using 8-cyclopropyl-6-ethynyl-3,4-dihydro-4,4-dimethylspiro[2H-1-benzopyran-2,1′-cyclopropane] (Intermediate 44, 0.03 g, 0.11 mmol), methyl-2-fluoro-4-iodo-benzoate (Reagent G, 0.025 g, 0.09 mmol), triethyl amine (3 mL), tetrahydrofuran (3 mL), dichlorobis(triphenylphosphine)palladium(II) (0.06 g, 0.085 mmol) followed by preparative normal phase HPLC using 10% ethyl acetate in hexane as the mobile phase, the title compound was obtained as a white solid (0.019 g, 40%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06359135B1
Source datasetuspto-grants-2002_03
ORD IDord-f07442ccaaf443b1ac28ed4dc1d9f219
Source noteuspto-grants-2002_03