Sodium Cyanide → 7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile

Participants

Role	Name	HCID	Charge
Reactant	Sodium Cyanide	HCID 8929	—
Reactant	HCID 11560384	HCID 11560384	—
Reactant	Ethyl acetate hexane	HCID 21226206	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418397	HCID 178418397	—
Solvent	Acetonitrile	HCID 6342	—
Product	7-Methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile	HCID 57949363	95%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 5-bromo-7-methyl-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-isoindol-1-one (0.600 g, 1.5 mmol), Pd(PPh3)4 (0.175 g, 0.14 mmol), sodium cyanide (0.163 g, 3.4 mmol), and CuI (0.029 g, 0.15 mmol) in acetonitrile (6 mL) was stirred at 80° C. for 18 h. Workup and silica gel column chromatography using 2:1 hexanes-ethyl acetate (typically 2:1 hexane-EtOAc) afforded 7-methyl-1-oxo-2-(4-trifluoromethoxy-benzyl)-2,3-dihydro-1H-isoindole-5-carbonitrile (0.491 g, 95%). 1H NMR (300 MHz, CDCl3): δ (ppm) 2.78 (s, 3H), 4.26 (s, 2H), 4.79 (s, 2H), 7.18 (d, 2H), 7.35 (d, 2H), 7.52 (s, 2H).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07968570B2
Source dataset	uspto-grants-2011_06
ORD ID	ord-3aacc735108247b59090dbb663adcee1
Source note	uspto-grants-2011_06