5-Bromo-7-methyl-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one → 7-Methyl-2-(4-chloro-benzyl)-5-[3-(4-methyl-piperazin-1-yl)-prop-1-ynyl)-2,3-dihydro-isoindol-1-one

Participants

Role	Name	HCID	Charge
Reactant	5-Bromo-7-methyl-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one	HCID 11681837	—
Reactant	1-Methyl-4-(prop-2-yn-1-yl)piperazine	HCID 13514091	—
Reactant	Chloroform methanol	HCID 21584188	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Solvent	Diisopropylamine	HCID 7912	—
Product	7-Methyl-2-(4-chloro-benzyl)-5-[3-(4-methyl-piperazin-1-yl)-prop-1-ynyl)-2,3-dihydro-isoindol-1-one	HCID 57949416	81.7%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of 1-methyl-4-prop-2-ynyl-piperazine (0.061 mL, 0.4 mmol), 5-bromo-7-methyl-2-(4-chloro-benzyl)-2,3-dihydro-isoindol-1-one (0.105 g, 0.3 mmol), PdCl2(PPh3)2 (0.011 g, 0.015 mmol), and CuI (0.0028 g, 0.015 mmol) in diisopropylamine (4 mL) was stirred at 100° C. for 2 h. Workup and silica gel column chromatography using 10:1 CHCl3-MeOH afforded 7-methyl-2-(4-chloro-benzyl)-5-[3-(4-methyl-piperazin-1-yl)-prop-1-ynyl)-2,3-dihydro-isoindol-1-one (0.100 g, 81%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07968570B2
Source dataset	uspto-grants-2011_06
ORD ID	ord-58e69559fc414362b0f2eb2662fc6582
Source note	uspto-grants-2011_06