Potassium Carbonate → benzyl 4-((R)-2-((6-(2-cyanophenyl)-2-(2-(tetrahydro-2H-pyran-2-yl)ethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate

https://huagongshe.com/reaction/2080304

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	2-Cyanophenylboronic acid	HCID 2734610	—
Reactant	benzyl 4-((R)-2-((6-chloro-2-(2-(tetrahydro-2H-pyran-2-yl)ethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate	HCID 57542717	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	benzyl 4-((R)-2-((6-(2-cyanophenyl)-2-(2-(tetrahydro-2H-pyran-2-yl)ethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate	HCID 57542296	77%

Reaction Conditions

Temperature	125 °C

Reaction Steps

A mixture of benzyl 4-((R)-2-((6-chloro-2-(2-(tetrahydro-2H-pyran-2-yl)ethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate (62 mg, 0.101 mmol), 2-cyanophenyl boronic acid (23 mg, 0.156 mmol), PdCl2(dppf)2 (11 mg, 0.02 mmol), K2CO3(92 g, 0.667 mmol) and anhydrous DMF (1 mL) was stirred at 125° C. for 1 hr. The mixture was filtered through the silica gel pad and washed with EtOAc. The filtrate was concentrated to dryness and purified on RP-HPLC using a mixture of acetonitrile and H2O to give benzyl 4-((R)-2-((6-(2-cyanophenyl)-2-(2-(tetrahydro-2H-pyran-2-yl)ethylamino)nicotinamido)methyl)pyrrolidin-1-yl)-4-oxobutylcarbamate (50 mg, 77%). LRMS (M+H+) m/z 653.3.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07932270B2
Source dataset	uspto-grants-2011_04
ORD ID	ord-aaf6166adf3a44ac8f4513283245a134
Source note	uspto-grants-2011_04