HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 3-phenyl-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Phenylboronic Acid | HCID 66827 | — |
| Reactant | HCID 178506572 | HCID 178506572 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethoxyethane ethanol | HCID 20074477 | — |
| Product | 3-phenyl-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine | HCID 71253684 | 60.2% |
Reaction Steps
To a solution of 3-iodo-5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridine from Example 4 (161 mg, 0.5 mmol) in DME:EtOH (5:1, 5 mL) was added Pd(dppf)Cl2 (20 mg), saturated solution of Na2CO3 (1 mL) and phenylboronic acid (74 mg, 0.6 mmol). The mixture was heated in argon under microwave radiation at 135 for 60 min. 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 116 (82 mg, 60%). 1H NMR (400 MHz, DMSO) δ 9.33 (s, 1H), 9.21 (s, 1H), 8.56 (s, 1H), 8.53-8.51 (m, 2H), 8.12-8.10 (m, 2H), 7.57-7.44 (m, 4H). ESI MS m/z=273.7 (M+1
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09260425B2 |
| Source dataset | uspto-grants-2016_02 |
| ORD ID | ord-3fbda996044a4306acc6c59dc859868e |
| Source note | uspto-grants-2016_02 |