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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2195488Generated: October 29, 2026

Methanesulfonic Acid → 6-Bromo-5-(2-fluoro-4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

https://huagongshe.com/reaction/2195488

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanesulfonic AcidHCID 6395—
Reactant3,4-dihydro-2H-pyranHCID 8080—
ReactantSodium BicarbonateHCID 516892—
Reactant6-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazoleHCID 66767153—
SolventTetrahydrofuranHCID 8028—
SolventEthyl AcetateHCID 8857—
Product6-Bromo-5-(2-fluoro-4-nitrophenoxy)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleHCID 6676690389%

Reaction Steps

To a solution of 6-bromo-5-(2-fluoro-4-nitrophenoxy)-1H-indazole (5.0 g, 14.2 mmol) in THF (50 mL) is added DHP (2.4 g, 28.5 mmol) and CH3SO3H (1.0 g, 10.4 mmol). The resulting mixture is stirred at RT for 1 hour. Then EtOAc and aqueous NaHCO3 solutions are added. The organic phase is separated, dried over anhydrous MgSO4, filtered and concentrated. The residue is purified by silica gel column chromatography eluting with PE:EtOAc (5:1) to give the desired product (5.5 g, 89.0% yield). MS (m/z): 436.0 (M+H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUSRE043878E1
Source datasetuspto-grants-2012_12
ORD IDord-7ee90691962446b7a97d565705f7a664
Source noteuspto-grants-2012_12