N,N-Dimethylpropargylamine → 7-Chloro-5-(3-dimethylamino-prop-1-ynyl)-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one

Participants

Role	Name	HCID	Charge
Reactant	N,N-Dimethylpropargylamine	HCID 81643	—
Reactant	Chloroform methanol	HCID 21584188	—
Reactant	5-Bromo-7-chloro-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one	HCID 57949670	—
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-Chloro-5-(3-dimethylamino-prop-1-ynyl)-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one	HCID 57949318	79%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of dimethyl-prop-2-ynyl-amine (0.036 mL, 0.32 mmol), 5-bromo-7-chloro-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.120 g, 0.28 mmol), PdCl2(PPh3)2 (0.011 g, 0.015 mmol), and CuI (0.0028 g, 0.015 mmol) in diisopropyl amine (4 mL) was stirred at 100° C. for 2 h. Workup and silica gel column chromatography using 10:1 CHCl3-MeOH afforded 7-chloro-5-(3-dimethylamino-prop-1-ynyl)-2-(4-phenoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.095 g, 79%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.36 (s, 6H), 3.46 (s, 2H), 4.23 (s, 2H), 4.76 (s, 2H), 6.93-7.38 (m, 10H), 7.43 (s, 1H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07968570B2
Source dataset	uspto-grants-2011_06
ORD ID	ord-d6ceacd95e9642c0934dd1acbc24730d
Source note	uspto-grants-2011_06