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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1528098Generated: October 30, 2026

Sodium Carbonate → HCID 57520093, compound

https://huagongshe.com/reaction/1528098

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
ReactantTert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 4642098—
ReactantHCID 57519920HCID 57519920—
CatalystHCID 178418397HCID 178418397—
SolventDimethylformamideHCID 6228—
ProductHCID 57520093HCID 57520093106.7%

Reaction Conditions

Temperature80 °C

Reaction Steps

1.500 g of 1-(6-bromo-quinolin-4-yl)-3-(6-trifluoromethyl-pyridin-2-yl)-urea (3.65 mmol), 1.692 g of tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5,6-dihydropyridine-1(2H)-carboxylate (5.47 mmol), 0.422 g of tetrakis(triphenylphosphine)palladium(0) (0.365 mmol) and 8.21 ml of a 2M sodium carbonate solution (16.42 mmol) were dissolved/suspended in 32 ml DMF in a microwave vessel, flushed with vacuum/argon, and subsequently heated in the microwave for 1 h at 80° C. HPLC/MSD indicated almost complete formation of the desired product. The reaction mixture was poured on ice, stirred for 1 h, and the precipitation formed was filtered off and dried in vacuum for 24 h. 2 g of the desired product were obtained as an off white powder (yield: quant.). The quite pure raw material was used without further purification in the next step.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09090592B2
Source datasetuspto-grants-2015_07
ORD IDord-30ef35c5acb143e7916f9267ed84eed7
Source noteuspto-grants-2015_07