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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 923662Generated: November 2, 2026

Sodium Carbonate → HCID 131734996, compound

https://huagongshe.com/reaction/923662

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium CarbonateHCID 10340—
Reactant1,4-DioxaneHCID 31275—
Reactant(1-Methyl-1H-indazol-7-yl)boronic acidHCID 44118216—
Reactanttert-butyl-N-{1-[(4-bromo-5-chloro-6-{2-[tris(propan-2-yl)silyl]ethynyl}-pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamateHCID 123381143—
CatalystPalladium ChlorideHCID 24290—
CatalystFerrocene-1,1'-bis-(diphenylphosphine)HCID 635956—
SolventWaterHCID 962—
ProductHCID 131734996HCID 131734996—

Reaction Conditions

Temperature100 °C

Reaction Steps

1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (20 mg, 0.03 mmol) is added to a mixture of tert-butyl-N-{1-[(4-bromo-5-chloro-6-{2-[tris(propan-2-yl)silyl]ethynyl}-pyridin-2-yl)carbamoyl]ethyl}-N-methylcarbamate C2 (82 mg, 0.14 mmol), (1-methyl-1H-indazol-7-yl)boronic acid (24 mg, 0.14 mmol), Na2CO3 (44 mg, 0.42 mmol), dioxane (0.8 ml) and water (0.2 ml) under argon atmosphere and stirred at 100° C. for 4 h. The mixture is diluted with water (10 ml) and extracted with EtOAc. The combined organic layers are dried over MgSO4 and concentrated in vacuo. The product is purified by RP HPLC. Yield: 25 mg (28%). HPLC-MS: M+H=624; tR=1.94 min (METHOD—1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09278978B2
Source datasetuspto-grants-2016_03
ORD IDord-1c681887f67341188b475b9338c8185f
Source noteuspto-grants-2016_03