Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 3-ethynyl-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine | HCID 58404690 | — |
| Reactant | HCID 67207288 | HCID 67207288 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 58404650 | HCID 58404650 | — |
Reaction Steps
To a mixture of 3-ethynyl-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine (20 mg, 0.080 mmol), 5-ethyl-4-iodo-1-phenyl-1H-pyrazole (24 mg, 0.08 mmol), copper (I) iodide (4.5 mg, 0.024 mmol), and tetrakis(triphenylphosphine)palladium (0) (9.2 mg, 0.0079 mmol) in N,N-dimethylformamide (2 ml), was added triethylamine (0.022 ml, 0.16 mmol). The mixture was sparged with argon for 3 minutes and heated to 70° C. After 1 h, reaction mixture was purified directly by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA to give 3-[(5-ethyl-1-phenyl-1H-pyrazol-4-yl)ethynyl]-4-methoxy-6-(1-methyl-1H-pyrazol-4-yl)pyrazolo[1,5-a]pyridine.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08455477B2 |
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| Source dataset | uspto-grants-2013_06 |
|---|
| ORD ID | ord-834f0eb589a7473b80334fa35a06fe08 |
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| Source note | uspto-grants-2013_06 |
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