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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2075713Generated: October 30, 2026

Sodium Azide → 7-[3-Fluoro-5-(4-methoxy-tetrahydro-pyran-4-yl)-phenoxymethyl]-1,2,3,9b-tetraaza-cyclopenta[a]naphthalene

https://huagongshe.com/reaction/2075713

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium AzideHCID 33557—
ReactantHCID 86613830HCID 86613830—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
Product7-[3-Fluoro-5-(4-methoxy-tetrahydro-pyran-4-yl)-phenoxymethyl]-1,2,3,9b-tetraaza-cyclopenta[a]naphthaleneHCID 67090988—

Reaction Conditions

Temperature130 °C

Reaction Steps

To 9b (29 mg, 0.07 mmol) in DMF (1 mL) was added sodium azide (9 mg, 0.09 mmol). The reaction was heated at 130° C. overnight, then cooled to room temperature and diluted with EtOAc and water. The aqueous layer was extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated. The crude material was purified by silica gel chromatography (50% EtOAc in hexanes) to give the desired product, 9c.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07919621B2
Source datasetuspto-grants-2011_04
ORD IDord-e377cd0d9e4740b89695f8edfdc11941
Source noteuspto-grants-2011_04