Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1851087Generated: November 1, 2026

Methanol → 4-(5-Bromopyrrolo[1,2-b]pyridazin-4-yloxy)-3-fluoroaniline

https://huagongshe.com/reaction/1851087

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMethanolHCID 887—
ReactantAmmonium ChlorideHCID 25517—
ReactantHCID 58368367HCID 58368367—
CatalystZincHCID 23994—
SolventTetrahydrofuranHCID 8028—
Product4-(5-Bromopyrrolo[1,2-b]pyridazin-4-yloxy)-3-fluoroanilineHCID 5836836293.7%

Reaction Conditions

Temperature70 °C

Reaction Steps

Methanol (1.2 mL), zinc powder (300 mg, 4.57=1) and ammonium chloride (130 mg, 2.47 mmol) were sequentially added to a solution of 5-bromo-4-(2-fluoro-4-nitrophenoxy)pyrrolo[1,2-b]pyridazine (67 mg, 0.19 mmol) in tetrahydrofuran (4.7 mL) and heated at 70° C. for 1.5 hours. Upon completion of the reaction, the resulting reaction mixture was cooled to room temperature and filtered by passing through a celite pad. The filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel chromatography (1-6% ethyl acetate in dichloromethane) to give the target compound (57 mg, 0.178 mmol, 93% yield).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08957102B2
Source datasetuspto-grants-2015_02
ORD IDord-523771a08dd9416c9a9d409d3a8c2809
Source noteuspto-grants-2015_02