Dimethylformamide → {3-[7-(3-Diethylamino-prop-1-ynyl)-5,5-dioxo-5H-5lambda6-dibenzothiophen-3-yl]-prop-2-ynyl}-diethylamine

Participants

Role	Name	HCID	Charge
Reactant	Dimethylformamide	HCID 6228	—
Reactant	Triethylamine	HCID 8471	—
Reactant	Dietylaminopropin	HCID 20010	—
Reactant	3,7-Dibromo-dibenzothiophene 5,5-dioxide	HCID 4071898	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418903	HCID 178418903	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	{3-[7-(3-Diethylamino-prop-1-ynyl)-5,5-dioxo-5H-5lambda6-dibenzothiophen-3-yl]-prop-2-ynyl}-diethylamine	HCID 67163580	82%

Reaction Conditions

Temperature	65 °C

Reaction Steps

A mixture of 3,7-dibromodibenzothiophene 5,5-dioxide (0.33 g, 0.88 mmol; see J. Med. Chem. 1978, 21, 1084), 3-diethylamino-1-propyne (0.5 mL, 3.4 mmol; Lancaster), triethylamine (0.6 mL, 4.2 mmol; Acros), dichlorobis(triphenylphosphino)palladium(II) (Cl2Pd(PPh3)2; 25 mg, 0.035 mmol; Aldrich), and copper(I) iodide (38 mg, 0.20 mmol; Aldrich) in DMF (10 mL) was heated to 65° C. for 60 h. The reaction mixture was diluted with EtOAc, washed with water and brine, and dried over Na2SO4. The residue was purified by chromatography (16 g silica gel, 2-7% gradient MeOH in CH2Cl2to afford the title compound (0.31 g, 0.71 mmol, 82% yield): MS (DCl/NH3) m/z 435 (M+H)+.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07365193B2
Source dataset	uspto-grants-2008_04
ORD ID	ord-b40e7644f83343a7a88643ebda83fd87
Source note	uspto-grants-2008_04