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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 531536Generated: October 31, 2026

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

https://huagongshe.com/reaction/531536

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant4-(4-tert-Butoxycarbonylpiperazinyl)phenylboronic acid, pinacol esterHCID 2795514—
Reactant5-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 118200974—
SolventWater 1,2-dimethoxyethaneHCID 18180031—
Producttert-butyl 4-(4-(3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridin-5-yl)phenyl)piperazine-1-carboxylateHCID 9003069759.47%

Reaction Steps

Using similar reaction conditions as described in step-ii of example-1, 5-bromo-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (compound of step-i of example-9) (200 mg, 0.53 mmol) was coupled with tert-butyl 4-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)piperazine-1-carboxylate (intermediate 40) (251 mg, 0.64 mmol) in sodium carbonate (168 mg, 1.59 mmol) PdCl2 (dppf) (19 mg, 0.0265 mmol), 1,2-Dimethoxyethane/water (25/3 ml) to afford 160 mg (59.47% yield) of the titled compound. MS: m/z=707.1 (M+1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09353107B2
Source datasetuspto-grants-2016_05
ORD IDord-8f79d86d529c42d5898ad7118587042c
Source noteuspto-grants-2016_05