Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | HCID 67374188 | HCID 67374188 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 67207569 | HCID 67207569 | — |
Reaction Steps
3-iodo-4-methoxy-6-phenylpyrazolo[1,5-a]pyridine (25.0 mg, 0.071 mmol), sodium cyanide (7.0 mg, 0.14 mmol), tetrakis(triphenylphosphine)palladium (0) (4.1 mg, 0.004 mmol), and copper (I) iodide (1.4 mg, 0.007 mmol) were added to a dry flask. Acetonitrile (2 ml) was added and the mixture was sparged with argon for 3 minutes, then heated to 65° C. After 16 h, the reaction mixture cooled and purified by preparative HPLC Reverse phase (C-18), eluting with acetonitrile/water+0.05% TFA to give 4-methoxy-6-phenylpyrazolo[1,5-a]pyridine-3-carbonitrile. 1H NMR (600 MHz, DMSO-d6) δ 8.66 (d, 1H); 8.58 (s, 1H); 7.82 (d, 2H); 7.49 (d, 2H); 7.41 (m, 1H); 7.31 (s, 1H); 4.08 (s, 3H). LRMS (ESI) calculated for C15H12N3O [M+H]+, 250.1; found 250.0.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08455477B2 |
|---|
| Source dataset | uspto-grants-2013_06 |
|---|
| ORD ID | ord-3c9847cf688e4cd7a1b518d367bb8b34 |
|---|
| Source note | uspto-grants-2013_06 |
|---|
