Ethanolamine → N-cyclopropyl-4-[4-(2-hydroxy-ethylamino)-imidazo[1,2-a]quinoxalin-1-yl]-benzamide

Participants

Role	Name	HCID	Charge
Reactant	Ethanolamine	HCID 700	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	(4-(Cyclopropylcarbamoyl)phenyl)boronic acid	HCID 2773359	—
Reactant	1-Bromo-4-chloroimidazo[1,2-A]quinoxaline	HCID 71741639	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Potassium Carbonate	HCID 11430	—
Product	N-cyclopropyl-4-[4-(2-hydroxy-ethylamino)-imidazo[1,2-a]quinoxalin-1-yl]-benzamide	HCID 49802724	13%

Reaction Conditions

Temperature	170 °C

Reaction Steps

(1-bromo-4-chloro-imidazo[1,2-a]quinoxaline (intermediate example 1.1, 1 mL, 0.2M in NMP), 2-amino-ethanol (2 eq, 0.8 mL, 0.5 M in NMP) and DIPEA (3 eq, 103 μL) were combined in a sealed vial and heated at 170° C. under microwave irradiation for 60 min. After cooling, [4-[(cyclopropylamino)carbonyl]phenyl]-boronic acid (1.5 eq, 0.3 mL, 1 M in NMP), Pd(dppf)Cl2 (0.1 eq, 533 μL, 0.0375 M in NMP) and potassium carbonate (600 μL, 1M in water) were added and the mixture was heated at 140° C. under microwave irradiation for 40 min. After cooling, the solution was filtered and subjected to preparative HPLC to give N-cyclopropyl-4-[4-(2-hydroxy-ethylamino)-imidazo[1,2-a]quinoxalin-1-yl]-benzamide (10.19 mg, 13%): UPLC-MS: RT==0.82 min; m/z (ES+) 388.4 [MH+]; required MW=387.4.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08729082B2
Source dataset	uspto-grants-2014_05
ORD ID	ord-6fb52968d7484460890fb5f7b2b3155c
Source note	uspto-grants-2014_05