Potassium Carbonate → tert-Butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate

https://huagongshe.com/reaction/2205610

Participants

Role	Name	HCID	Charge
Reactant	Potassium Carbonate	HCID 11430	—
Reactant	tert-Butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate	HCID 15836637	—
Reactant	Benzyl (S)-(1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate	HCID 118214750	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Dimethylformamide	HCID 6228	—
Product	tert-Butyl (S)-3-(5-(1-(((benzyloxy)carbonyl)amino)ethyl)-1-methyl-1H-pyrrolo[3,2-b]pyridin-6-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate	HCID 118214749	87%

Reaction Conditions

Temperature	100 °C

Reaction Steps

A mixture of benzyl (S)-(1-(6-bromo-1-methyl-1H-pyrrolo[3,2-b]pyridin-5-yl)ethyl)carbamate (850 mg, 2.19 mmol), tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-2,5-dihydro-1H-pyrrole-1-carboxylate (904 mg, 3.06 mmol), K2CO3 (605 mg, 4.38 mmol) and Pd(dppf)Cl2 (170 mg, 0.22 mmol) in anhydrous DMF (25 mL) was stirred at 100° C. for 5 hours under nitrogen. After the solvent was removed, the residue was purified by silica gel column chromatography (PE/EtOAc=7:1) to give the title compound as a yellow oil (900 mg, 87%). ESI-MS m/z [M+H]+ calc'd for C22H32N4O4, 477. found 477.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09371321B2
Source dataset	uspto-grants-2016_06
ORD ID	ord-ff605ea019984e709d141fa17965776b
Source note	uspto-grants-2016_06