Sodium Carbonate → tert-butyl 5-(3-(methylsulfonamido)phenyl)-3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	1H-Pyrazole, 1-[(3-nitrophenyl)methyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-	HCID 90030904	—
Reactant	tert-butyl 3-iodo-5-(3-(methylsulfonamido)phenyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate	HCID 90031437	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Water 1,2-dimethoxyethane	HCID 18180031	—
Product	tert-butyl 5-(3-(methylsulfonamido)phenyl)-3-(1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate	HCID 118523971	68%

Reaction Steps

Using similar reaction conditions as described in step-i of example 1, tert-butyl 3-iodo-5-(3-(methylsulfonamido)phenyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (intermediate-32) (300 mg, 0.5 mmol) was coupled with 1-(3-nitrobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 10) (211 mg, 0.6 mmol) in sodium carbonate (189 mg, 1.7 mmol), PdCl2(dppf) (20 mg, 0.02 mmol) and DME/water (3/3 ml) to afford 200 mg (59% yield) of the pure product after column purification using 30% ethyl acetate in hexane as eluent.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-c6c56c1d34504ac68dbf6489ef694ff2
Source note	uspto-grants-2016_05