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

Participants

Role	Name	HCID	Charge
Reactant	Sodium Carbonate	HCID 10340	—
Reactant	tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate	HCID 90030611	—
Reactant	3,5-dimethyl-1-(3-nitrobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 90030725	—
Catalyst	Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)	HCID 178418228	—
Solvent	Ethanol toluene water	HCID 86587398	—
Product	tert-butyl 4-(4-(3-(3,5-dimethyl-1-(3-nitrobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate	HCID 118524012	43.8%

Reaction Steps

Using similar reaction conditions as described in step-ii of intermediate 1, tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (intermediate 41) (400 mg, 0.6 mmol) was coupled with 3,5-dimethyl-1-(3-nitrobenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 56) (240 mg, 0.66 mmol) in sodium carbonate (196 mg, 1 mmol), PdCl2(dppf) (22 mg, 0.03 mmol), toluene/ethanol/water (2/2/2 ml) to give 200 mg (43% yield) of titled compound after purification by column (SiO2) using 30% ethyl acetate in hexane as eluent. MS: m/z=762.3 (M+1).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-0614b900772b42a4b597f33c8414782f
Source note	uspto-grants-2016_05