Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1054836Generated: November 1, 2026

Triethylamine → HCID 86698827, compound

https://huagongshe.com/reaction/1054836

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantPhenylacetyleneHCID 10821—
Reactantmethyl 5-bromo-6-chloro-1H-indazole-3-carboxylateHCID 86698828—
CatalystCopper iodideHCID 83717—
CatalystHCID 178418397HCID 178418397—
SolventTetrahydrofuranHCID 8028—
ProductHCID 86698827HCID 8669882737.9%

Reaction Conditions

Temperature120 °C

Reaction Steps

A mixture of methyl 5-bromo-6-chloro-1H-indazole-3-carboxylate (50 mg, 0.17 mmol), triethylamine (0.05 mL, 0.4 mmol), tetrakis(triphenylphosphine)palladium(0) (10.7 mg, 0.009 mmol), copper iodide (3.0 mg, 0.017 mmol) and phenyl acetylene (20 mg, 0.20 mmol) in tetrahydrofuran (1.0 mL) was sealed and heated to 120° C. for 16 hours. The cooled reaction mixture was concentrated in vacuo and purified by flash chromatography utilizing heptanes/ethyl acetate (1:1 to 0:1) to give the title compound (20 mg) as a yellow solid. MS (ES−): 309.0 (M−H)− Step 2

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09394285B2
Source datasetuspto-grants-2016_07
ORD IDord-930ebe6c8c5b4179b4563fd3e8eb3e87
Source noteuspto-grants-2016_07