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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 531542Generated: October 31, 2026

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

https://huagongshe.com/reaction/531542

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactanttert-butyl 4-(4-(3-iodo-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylateHCID 90030611—
Reactant1-[(2,5-Difluorophenyl)methyl]-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1h-pyrazoleHCID 90031187—
CatalystHCID 178418476HCID 178418476—
SolventEthanol toluene waterHCID 86587398—
Producttert-butyl 4-(4-(3-(1-(2,5-difluorobenzyl)-3,5-dimethyl-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylateHCID 90033968125.7%

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) (160 mg, 0.243 mmol) was coupled with 1-(2,5-difluorobenzyl)-3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (intermediate 25) (85 mg, 0.243 mmol) in sodium carbonate (77 mg, 0.729 mmol), Pd(PPh3)2Cl2 (17 mg, 0.0243 mmol), Toluene/ethanol/water (15/7.5/1 ml) to give 230 mg of titled compound. MS: m/z=753.1 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09353107B2
Source datasetuspto-grants-2016_05
ORD IDord-5e44f0af532e467da6c6702d641c2c9a
Source noteuspto-grants-2016_05