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

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	2-(4-Methylpiperazin-1-yl)pyridine-4-boronic acid, pinacol ester	HCID 2769537	—
Reactant	(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide	HCID 86621691	—
Solvent	1,2-Dimethoxyethane	HCID 8071	—
Product	(E)-3-(1-{4-[2-(4-Methyl-piperazin-1-yl)-pyridin-4-yl]-benzenesulfonyl}-1H-pyrrol-3-yl)-N-(tetrahydro-pyran-2-yloxy)-acrylamide	HCID 86621699	64.3%

Reaction Conditions

Temperature	100 °C

Reaction Steps

(E)-3-[1-(4-Bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-N-(tetrahydro-pyran-2-yloxy)-acrylamide (6.8 g) and 1-methyl-4-[4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-pyridin-2-yl]-piperazine (5.0 g) are dissolved in DME (300 mL). Under an inert gas atmosphere are added (Ph3P)3PdCl2 (2.1 g) and 2M Na2CO3-solution (44 mL). The mixture is heated to 100° C. for 2.5 h. After filtration and extraction, the crude product from the organic phase is purified by silica gel flash chromatography. By means of chloroform/EtOH (30:1-19:1). 5.3 g of the title compound are obtained as brownish oil.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08815855B2
Source dataset	uspto-grants-2014_08
ORD ID	ord-8a9212e4ca1e49f48d70e64d04814f11
Source note	uspto-grants-2014_08