3,3-Dimethyl-1-butyne → 2-{2-[4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-ethanesulfonylamino}-5-methyl-benzenesulfonamide

Participants

Role	Name	HCID	Charge
Reactant	3,3-Dimethyl-1-butyne	HCID 13512	—
Reactant	Diisopropylethylamine	HCID 81531	—
Reactant	2-[2-(4-Bromo-phenyl)-ethanesulfonylamino]-5-methyl-benzenesulfonamide	HCID 57750964	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	2-{2-[4-(3,3-Dimethyl-but-1-ynyl)-phenyl]-ethanesulfonylamino}-5-methyl-benzenesulfonamide	HCID 57750926	25.6%

Reaction Conditions

Temperature	80 °C

Reaction Steps

A mixture of 2-[2-(4-bromo-phenyl)-ethanesulfonylamino]-5-methyl-benzenesulfonamide (0.08 g, 0.18 mmol), N,N-diisopropylethylamine (0.1 mL, 0.55 mmol), and copper(I) iodide (7 mg, 0.04 mmol) in anhydrous N,N-dimethylformamide (2 mL) was degassed with nitrogen for 30 min. (1,1′-Bis(diphenylphosphino)ferrocene)-dichloropalladium(II) (14 mg, 0.02 mmol) and 3,3-dimethyl-1-butyne (0.045 mL, 0.37 mmol) were added and the reaction mixture was heated in a sealed tube at 80° C. overnight. The reaction mixture was diluted with ethyl acetate (20 mL), washed with water and brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by preparative TLC, using 5% methanol in dichloromethane as the eluent, to give 20 mg (25% yield) of the title compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09145380B2
Source dataset	uspto-grants-2015_09
ORD ID	ord-c64f3222e86a43f8ac9ccac19f7c0cbc
Source note	uspto-grants-2015_09