Tetrahydrofuran → HCID 90093834, compound

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	1,8-Diazabicyclo(5.4.0)undec-7-ene	HCID 81184	—
Reactant	(1R)-(+)-1-(4-Fluorophenyl)ethylamine	HCID 6950187	—
Reactant	HCID 118558145	HCID 118558145	—
Catalyst	Molybdenum carbonyl (Mo(CO)6)	HCID 98885	—
Catalyst	palladium(II) acetate	HCID 167845	—
Product	HCID 90093834	HCID 90093834	—

Reaction Conditions

Temperature	150 °C

Reaction Steps

DBU (4.50 equiv.) was added to a stirred, capped mixture of methyl 5-(2-benzyl-6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate (1 eq), Pd(OAc)2 (0.05 equiv.), molybdenum hexacarbonyl (1.0 equiv.) and (R)-1-(4-fluorophenyl)ethylamine (1.20 equiv.) in THF (0.2 M) and the mixture was stirred at 150° C. for 30 min. in a microwave. The mixture was purified by preparative TLC [1 mm] eluting with 50% EtOAc/hexanes to afford (R)-methyl 5-(2-benzyl-6-((1-(4-fluorophenyl)ethyl)carbamoyl)-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09290454B2
Source dataset	uspto-grants-2016_03
ORD ID	ord-99a6ad020f6f49c78a3871132b6d01a9
Source note	uspto-grants-2016_03