Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | HCID 178434364 | HCID 178434364 | — |
| Reactant | HCID 178514837 | HCID 178514837 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 178434366 | HCID 178434366 | 15.1% |
Reaction Steps
To a solution of 5-Bromo-3-methyl-1H-pyrazolo[3,4-c]pyridine from Example 102 (106 mg, 0.5 mmol) in DMF (5 mL) was added Pd(dppf)Cl2 (20 mg), saturated solution of Na2CO3 (1 mL) and 1H-pyrazol-3-ylboronic acid (67 mg, 0.6 mmol). The mixture was stirred under argon for 16 h at 80° C. After cooling down, the solvent was removed under reduced pressure and the residue was purified by silica-gel column chromatography (mobile phase: EA:PE=1:1) to afford 103 (15 mg, 15%). 1H NMR (500 MHz, MeOD) δ 8.96 (s, 1H), 8.23 (s, 1H), 7.71 (s, 1H), 6.90 (d, J=1.5, 1H), 2.65 (s, 3H). ESI MS m/z=200.1 (M+1)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09260425B2 |
|---|
| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-5a0851e1f8ff434eb9fa5f8043d6e8a8 |
|---|
| Source note | uspto-grants-2016_02 |
|---|
