Sodium Carbonate → tert-butyl 4-(4-(3-(1-(3-chlorobenzyl)-3,5-dimethyl-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	1-[(3-Chlorophenyl)methyl]-3,5-dimethyl-4-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole	HCID 90031492	—
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-(1-(3-chlorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate	HCID 90030349	31.1%

Reaction Steps

Using similar reaction conditions as described in step-ii of example-1, tert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylate (intermediate 41) (200 mg, 0.3 mmol) was coupled with 1-(3-chlorobenzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 54) (107 mg, 0.33 mmol) in sodium carbonate (99 mg, 0.9 mmol), Pd(dppf)Cl2 (12 mg, 0.01 mmol), toluene/ethanol/water (2/2/1 ml) to give 70 mg (31% yield) of titled compound.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09353107B2
Source dataset	uspto-grants-2016_05
ORD ID	ord-34b7a4a711d744e389e22b5650092fa5
Source note	uspto-grants-2016_05