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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 588273Generated: October 30, 2026

Potassium Carbonate → HCID 90417056, compound

https://huagongshe.com/reaction/588273

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPotassium CarbonateHCID 11430—
Reactant5-Bromo-2-oxindoleHCID 611193—
ReactantTert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 4642098—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
SolventSodium BicarbonateHCID 516892—
ProductHCID 90417056HCID 90417056102.5%

Reaction Conditions

Temperature120 °C

Reaction Steps

To a suspension of 5-bromoindolin-2-one (600 mg, 2.83 mmol) in 1,4-Dioxane (9 ml) and H2O (3 ml) were added tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (1.05 g, 3.40 mmol), Pd(PPh3)4 (164 mg, 0.142 mmol) and K2CO3 (1.17 g, 8.50 mmol). After stirring at 120° C. in microwave reactor for 1 h, the reaction mixture was diluted with sat. NaHCO3 aq. and extracted with CHCl3. The organic layer was dried over Na2SO4 and concentrated. The residue was purified by column chromatography (CHCl3/MeOH) to give tert-butyl 4-(2-oxoindolin-5-yl)-5,6-dihydropyridine-1(2H)-carboxylate (912 mg) as mixture with triphenylphosphin oxide.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09227962B2
Source datasetuspto-grants-2016_01
ORD IDord-d5fc950e0e454d528c9bca429e1fc867
Source noteuspto-grants-2016_01