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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 338492Generated: October 30, 2026

Triethylamine → HCID 86698827, compound

https://huagongshe.com/reaction/338492

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantPhenylacetyleneHCID 10821—
Reactant1H-Indazole-3-carboxylic acid, 5-bromo-6-chloro-, methyl esterHCID 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 numberUS08889730B2
Source datasetuspto-grants-2014_11
ORD IDord-097b7ceb5713452590eb1453248ad68b
Source noteuspto-grants-2014_11