Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | 1H-Indazole-3-carboxylic acid, 5-bromo-6-chloro-, methyl ester | HCID 86698828 | — |
| Catalyst | Copper iodide | HCID 83717 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 86698827 | HCID 86698827 | 37.9% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08889730B2 |
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| Source dataset | uspto-grants-2014_11 |
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| ORD ID | ord-097b7ceb5713452590eb1453248ad68b |
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| Source note | uspto-grants-2014_11 |
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