1,2-Dimethoxyethane → 3-[(E)-2-(3,5-difluorophenyl)vinyl][1,4]benzodioxino[2,3-c]pyridazine

Participants

Role	Name	HCID	Charge
Reactant	1,2-Dimethoxyethane	HCID 8071	—
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	3-Chlorobenzo[5,6][1,4]dioxino[2,3-c]pyridazine	HCID 12213466	—
Reactant	(E)-2-(3,5-Difluorostyryl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane	HCID 16218219	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Water	HCID 962	—
Product	3-[(E)-2-(3,5-difluorophenyl)vinyl][1,4]benzodioxino[2,3-c]pyridazine	HCID 117691163	95.2%

Reaction Conditions

Temperature	100 °C

Reaction Steps

Under an argon atmosphere, to 3-chloro[1,4]benzodioxino[2,3-c]pyridazine (500 mg) were added 1,2-dimethoxyethane (7.5 ml), 2M aqueous sodium carbonate solution (3.0 mL), 2-[(E)-2-(3,5-difluorophenyl)vinyl]-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (720 mg) and tetrakis(triphenylphosphine)palladium (130 mg). The reaction mixture was stirred at 100° C. for 3 hr and cooled to room temperature. Water was added, and the obtained solid was collected by filtration and dried under reduced pressure to give 3-[(E)-2-(3,5-difluorophenyl)vinyl][1,4]benzodioxino[2,3-c]pyridazine (700 mg).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09212147B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-684b39ef67014aa2b8e4380ea36e39b1
Source note	uspto-grants-2015_12