Potassium Carbonate → 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-(2-methylpropyl)imidazo[1,2-a]quinoxalin-4-amine

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	(2,3-Dihydro-1,4-benzodioxin-6-yl)boronic acid	HCID 2776178	—
Reactant	(1-Bromo-imidazo[1,2-a]quinoxalin-4-yl)isobutyl-amine	HCID 66601580	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Product	1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-(2-methylpropyl)imidazo[1,2-a]quinoxalin-4-amine	HCID 49801875	22%

Reaction Conditions

Temperature	130 °C

Reaction Steps

0.1 mmol (1-bromo-imidazo[1,2-a]quinoxalin-4-yl)-isobutyl-amine (intermediate example 2.1, 1 mL, 0.1 M in NMP), 0.15 mmol 2,3-dihydro-1,4-benzodioxin-6-ylboronic acid (0.3 mL, 0.5 M in NMP, 1.5 eq), 0.02 mmol Pd(dppf)Cl2 (0.533 mL, 0.0375M in NMP, 0.2 eq) and 0.3 mmol K2CO3 (0.3 mL, 1M in water, 3 eq) were combined in a sealed vial and heated at 130° C. under microwave irradiation for 60 min. After cooling, the solution was filtered and subjected to preparative HPLC to give 8.1 mg (22%) 1-(2,3-dihydro-1,4-benzodioxin-6-yl)-N-(2-methylpropyl)imidazo[1,2-a]quinoxalin-4-amine. UPLC-MS: RT==1.26 min; m/z (ES+) 375.4 [MH+]; required MW=374.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08729082B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-d97bf9c4f1ec4398a05c3a21af71d2e1
Source note	uspto-grants-2014_05