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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 69237Generated: October 26, 2026

1,2-Dimethoxyethane → (Rac)-(5,7-difluoro-quinolin-6-yl)-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanol

https://huagongshe.com/reaction/69237

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1,2-DimethoxyethaneHCID 8071—
ReactantSodium CarbonateHCID 10340—
Reactant1-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 2773987—
Reactant(6-Chloroimidazo[1,2-b]pyridazin-3-yl)(5,7-difluoroquinolin-6-yl)methanolHCID 58147519—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
SolventEthyl AcetateHCID 8857—
Product(Rac)-(5,7-difluoro-quinolin-6-yl)-[6-(1-methyl-1h-pyrazol-4-yl)-imidazo[1,2-b]pyridazin-3-yl]-methanolHCID 68640982—

Reaction Conditions

Temperature150 °C

Reaction Steps

(rac)-(6-Chloro-imidazo[1,2-b]pyridazin-3-yl)-(5,7-difluoro-quinolin-6-yl)-methanol (Stage 171.3, 1.8 g, 5.19 mmol) was introduced in a microwave reactor together with 1-Methyl-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (1.08 g, 5.19 mmol), tetrakis(triphenylphosphine)-palladium (300 mg, 0.26 mmol), 2 M Na2CO3 (9.34 mL) and DME (20 mL). The mixture was heated at 150° C. under microwave irradiation for 50 min. The RM was taken up with EtOAc and washed with 10% Na2CO3 and brine. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with Et2O and the precipitate was filtered off to give the title compound as a black solid (tR 0.8 min (conditions 2), MH+=393)

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08822468B2
Source datasetuspto-grants-2014_09
ORD IDord-201dfbaf59554d55879f90002b554c57
Source noteuspto-grants-2014_09