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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1695783Generated: November 1, 2026

Sodium Carbonate → HCID 44541043, compound

https://huagongshe.com/reaction/1695783

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant1,4-DioxaneHCID 31275—
Reactant2-Methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamideHCID 58255833—
ReactantN-(5-bromo-2-methoxypyridin-3-yl)-2,4-difluorobenzenesulfonamideHCID 59859951—
CatalystBis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)HCID 178418228—
SolventWaterHCID 962—
ProductHCID 44541043HCID 4454104315.5%

Reaction Conditions

Temperature140 °C

Reaction Steps

N-[5-Bromo-2-(methyloxy)-3-pyridinyl]-2,4-difluorobenzenesulfonamide (39 mg, 0.104 mmol), 2-methyl-N-[2-(tetrahydro-2H-pyran-2-yl)-6-(4,4,6,6-tetramethyl-1,3,2-dioxaborinan-2-yl)-2H-indazol-4-yl]-1,3-thiazole-4-carboxamide (50 mg, 0.104 mmol), Pd(dppf)Cl2 (8 mg, 10.36 μmol) and sodium carbonate (44 mg, 0.415 mmol) were added to a microwave vial, followed by 1,4-Dioxane (0.5 mL) and Water (0.5 mL) and the reaction mixture was heated in the microwave at 140° C. for 20 min. After cooling, the mixture was then passed through a 1 g silica cartridge and washed with DCM:methanol. The solvent was evaporated by blow down under nitrogen. The residue was dissolved in 1.6 ml DMSO:methanol (1:1, v/v) and passed through a 1 g C18 cartridge, washing with acetonitrile, then evaporated by blow down. The residue was dissolved in 1.6 ml DMSO:methanol (1:1, v/v) and purified by MDAP (Method E). This MDAP purification step was then repeated to afford the title compound (9 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08163743B2
Source datasetuspto-grants-2012_04
ORD IDord-f147a6111ef14501a9b1f2ebd4923315
Source noteuspto-grants-2012_04