Sodium Carbonate → (E)-3-(1-{4'-[2-(4-Methyl-piperazin-1-yl)-ethoxy]-biphenyl-3-sulfonyl}-1H-pyrrol-3-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamide

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1-Methyl-4-{2-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]ethyl}piperazine	HCID 53440265	—
Reactant	(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide	HCID 86621698	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	(E)-3-(1-{4'-[2-(4-Methyl-piperazin-1-yl)-ethoxy]-biphenyl-3-sulfonyl}-1H-pyrrol-3-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamide	HCID 86621700	—

Reaction Conditions

Temperature	100 °C

Reaction Steps

(E)-3-[1-(3-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (7.9 g) and 1-methyl-4-{2-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenoxy]-ethyl}-piperazine (9.0 g) are dissolved in DME (300 mL). Under an inert gas atmosphere there are added (Ph3P)3PdCl2 (2.4 g) and 2M Na2CO3-solution (50 mL) and the mixture is heated to 100° C. for 2 h. The mixture is filtered, evaporated and the residue is treated with ethyl acetate and 5% solution of NaHCO3. The organic phase is dried and evaporated and the crude product is purified by silica gel flash chromatography. 5.7 g of the Ube compound are obtained.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07666868B2
Source dataset	uspto-grants-2010_02
ORD ID	ord-f0fbcaa1fb8c42efbd2a224f1aa9cffc
Source note	uspto-grants-2010_02