Ammonia → N-(2-{4-[(tert-Butyldimethylsilanyl)-ethynyl]-phenyl}-1-methyl-ethyl)-acetamide

Participants

Role	Name	HCID	Charge
Reactant	Ammonia	HCID 222	—
Reactant	Diisopropylamine	HCID 7912	—
Reactant	(tert-Butyldimethylsilyl)acetylene	HCID 2757281	—
Reactant	Trifluoromethanesulfonic acid 4-(2-acetylamino-propyl)-phenyl ester	HCID 86669624	—
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	Acetonitrile	HCID 6342	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Ethyl Acetate	HCID 8857	—
Product	N-(2-{4-[(tert-Butyldimethylsilanyl)-ethynyl]-phenyl}-1-methyl-ethyl)-acetamide	HCID 68181211	—

Reaction Steps

To 2.40 g (7.38 mmol) trifluoromethanesulfonic acid 4-(2-acetylamino-propyl)-phenyl ester (I53.1), 1.52 mL (8.12 mmol) (tert-butyldimethylsilyl)acetylene and 2.56 mL (18.4 mmol) diisopropylamine in 25 mL ACN are added 72.3 mg (0.089 mmol) [1,1′bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane and 17.2 mg (0.09 mmol) CuI, and the mixture is stirred at r.t. for 24 h. Again 0.69 mL (3.69 mmol) (tert-butyldimethyl-silyl)acetylene are added and stirring is continued for additional 24 h. The mixture is poured onto aq. ammonia solution (5%), diluted with EtOAc and the organic layer is separated. The organic layer is washed with diluted aq. ammonia solution (1×) and water (1×), dried with MgSO4 and the solvent is removed in vacuo. The residue is purified by column chromatography (silica gel; PE/EtOAc 2/8).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08835472B2
Source dataset	uspto-grants-2014_09
ORD ID	ord-09510df3e7fb4d3789ecb37e5c37b49d
Source note	uspto-grants-2014_09