Nitrogen → 3,5-Dimethyl-4-(1-oxo-indan-4-ylsulfanyl)-benzonitrile

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)	HCID 636044	—
Reactant	4-Bromo-3,5-dimethyl-benzonitrile	HCID 11085070	—
Reactant	4-Mercapto-2,3-dihydro-1H-inden-1-one	HCID 55297318	—
Solvent	1,4-Dioxane	HCID 31275	—
Product	3,5-Dimethyl-4-(1-oxo-indan-4-ylsulfanyl)-benzonitrile	HCID 118093733	87.9%

Reaction Conditions

Temperature	120 °C

Reaction Steps

4-Mercapto-indan-1-one (Step 1, 210 mg, 1.28 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (74 mg, 0.13 mmol), 4-bromo-3,5-dimethyl-benzonitrile (269 mg, 1.28 mmol) and diisopropylethylamine (0.88 mL, 5.1 mmol) are dissolved in 1,4-dioxane (2 mL). The mixture is degassed with N2, tris(dibenzylideneacetone)palladium(0) (117 mg, 0.13 mmol) added and heated under microwave irradiation at 120° C. for 2 hours. The solution is concentrated under vacuum. The crude product obtained is purified by flash chromatography (10-80% ethyl acetate in cyclohexane) to give the title compound (Yield: 330 mg). LC (METHOD 5): tR=1.36 min; Mass spectrum (ES+): m/z=294 [M+H]+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09308194B2
Source dataset	uspto-grants-2016_04
ORD ID	ord-025797879aef413bb6456330b55491ca
Source note	uspto-grants-2016_04