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HRID 1483783Erstellt: 25. Oktober 2026

Binap, (A+-)- → 4-((3-(3-(Trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-yl)oxy)cyclohexanol

https://huagongshe.com/reaction/1483783

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktBinap, (A+-)-HCID 634876—
EduktCyclohexane-1,1-diolHCID 19352763—
EduktPotassium tert-butoxideHCID 23665647—
Edukt6-Chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazineHCID 59379861—
KatalysatorBis(dibenzylideneacetone)palladiumHCID 9811564—
LösungsmittelTolueneHCID 1140—
LösungsmittelDichloromethane methanolHCID 21226129—
Produkt4-((3-(3-(Trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-yl)oxy)cyclohexanolHCID 6659815213,2%

Reaktionsbedingungen

Temperatur120 °C

Reaktionsschritte

A solution of 6-chloro-3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazine (0.3 g, 0.96 mmol) and cyclohexanediol (0.11 g, 0.96 mmol) in toluene 5 mL was added potassium tertiary butoxide (0.165 g, 1.72 mmol), rac-BINAP (36 mg, 0.057 mmol) and Pd2(dba)3 (26 mg, 0.029 mmol) and the mixture was heated at 120° C. for 4 h under microwave irridation. The resulting dark brown solution was cooled down and was concentrated under reduced pressure. The solid was further purified by using combiflash chromatography (12 g column), eluent: 0-10% methanol/DCM and obtained product 4-((3-(3-(trifluoromethoxy)phenyl)imidazo[1,2-b]pyridazin-6-yl)oxy)cyclohexanol (50 mg, 0.127 mmol, 13% yield).

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS09416132B2
Quelldatensatzuspto-grants-2016_08
ORD IDord-ad0d90485b5d46b2934ad8dba80ace05
Quellennotizuspto-grants-2016_08