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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2108755Generated: October 31, 2026

Potassium Carbonate → N-(3-Methoxybenzyl)-5-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamide

https://huagongshe.com/reaction/2108755

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 49758959—
ReactantN-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamideHCID 57421982—
CatalystTetrakis(triphenylphosphine)palladiumHCID 11979704—
SolventWaterHCID 962—
Solvent1,2-DimethoxyethaneHCID 8071—
SolventEthyl AcetateHCID 8857—
ProductN-(3-Methoxybenzyl)-5-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-3-yl)thiophene-3-carboxamideHCID 5763317245%

Reaction Steps

N-(3-Methoxybenzyl)-5-bromothiophene-3-carboxamide (100 mg, 0.3 mmol), 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (122 mg, 0.3 mmol), potassium carbonate (125 mg, 0.9 mmol), and tetrakis(triphenylphosphine) palladium (0) (20 mg) were combined in 4 mL DME, 1 mL water, and heated to 160° C. in the microwave for 10 minutes. The reaction mixture was diluted with EtOAc and water. The organic layer was filtered through celite and concentrated to an oil which was purified by column chromatography on silica (20 to 60% EtOAc/hexanes) to give the product as a brown oil, 0.07 g, 0.14 mmol, 45% yield. MH+ 518.0

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07514448B2
Source datasetuspto-grants-2009_04
ORD IDord-802ff1787b58405e8e331d338c9c74da
Source noteuspto-grants-2009_04