Cesium carbonate → Ethyl 2-(3-(cyclopropanecarboxamido)isoquinolin-7-yloxy)-2-methylpropanoate

Participants

Role	Name	HCID	Charge
Reactant	Cesium carbonate	HCID 10796	—
Reactant	Propanoic acid, 2-bromo-2-methyl-, ethyl ester	HCID 11745	—
Reactant	1,4-Dioxane	HCID 31275	—
Reactant	N-(7-hydroxyisoquinolin-3-yl)cyclopropanecarboxamide	HCID 67975011	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	Ethyl 2-(3-(cyclopropanecarboxamido)isoquinolin-7-yloxy)-2-methylpropanoate	HCID 67974885	80.5%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of N-(7-hydroxyisoquinolin-3-yl)cyclopropanecarboxamide (53 mg, 0.23 mmol), ethyl 2-bromoisobutyrate (69 uL, 0.47 mmol), cesium carbonate (166.8 mg, 0.5119 mmol), and 1,4-dioxane (2.0 mL, 26 mmol) was heated in a sealed vial at 100° C. for 22 hours. The reaction mixture was poured into ethyl acetate, washed with water and brine, dried over MgSO4, filtered, and evaporated in vacuo to yield 63.4 mg (80%) of ethyl 2-(3-(cyclopropanecarboxamido)isoquinolin-7-yloxy)-2-methylpropanoate which was carried forward without purification. LCMS (ESI): M+H=343.2.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09206175B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-5483d346cc284478bbf6f1342c592dda
Source note	uspto-grants-2015_12