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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1038126Generated: November 4, 2026

Cesium fluoride → HCID 86630183, compound

https://huagongshe.com/reaction/1038126

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium fluorideHCID 25953—
Reactant3-bromo-5-nitro-1-trityl-1H-indazoleHCID 58946443—
Reactant2-(1-Methoxy-1-methyl-ethyl)-4-tributylstannanyl-pyridineHCID 86630181—
CatalystCopper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)HCID 24350—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventDimethylformamideHCID 6228—
SolventEthyl AcetateHCID 8857—
ProductHCID 86630183HCID 86630183—

Reaction Conditions

Temperature120 °C

Reaction Steps

2-(1-methoxy-1-methyl-ethyl)-4-tributylstannanyl-pyridine 13AO (0.1 g, 0.24 mmol), 3-bromo-5-nitro-1-trityl-1H-indazole 1AJ (0.12 g, 0.24 mmol), CsF (0.08 g, 0.53 mmol), [Pd2(dba)3] (5 mg, 0.005 mmol), Pd[P(t-Bu)3)2, and CuI (4 mg, 0.024 mmol) in DMF (2 ml) was degassed for 5 minutes. Then it was heated at 120° C. for two hours. Cooled to room temperature and diluted with EtOAc (10 ml). It was then filtered on a celite pad. Filtrate was washed with water (3 ml) and the organic extracts were dried over MgSO4. It was filtered again on a celite pad and concentrated. The residue was purified on silica gel eluting with 1/3 EtOAc/Hexane to give the desired product 3-[2-(1-methoxy-1-methyl-ethyl)-pyridin-4-yl]-5-nitro-1-trityl-1H-indazole 14AO (0.05 g, 39%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08546404B2
Source datasetuspto-grants-2013_10
ORD IDord-27e4443fef8149b6805da2aa02726018
Source noteuspto-grants-2013_10