Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole | HCID 21931539 | — |
| Reactant | 5-Bromo-1H-pyrazolo[3,4-c]pyridine | HCID 45789778 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Dimethoxyethane ethanol | HCID 20074477 | — |
| Product | HCID 86676682 | HCID 86676682 | 22% |
Reaction Steps
To a solution of 5-bromo-1H-pyrazolo[3,4-c]pyridine (100 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 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (116 mg, 0.6 mmol). Under argon the mixture was stirred under microwave irradiation at 150° C. 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 5-(1H-pyrazol-4-yl)-1H-pyrazolo[3,4-c]pyridine (20 mg, 22%). 1H NMR (500 MHz, MeOD) δ 9.05 (s, 1H), 8.24 (m, 2H), 7.75 (s, 1H), 6.89 (s, 1H). ESI MS m/z=186.1 (M+1)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09260425B2 |
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| Source dataset | uspto-grants-2016_02 |
|---|
| ORD ID | ord-d22b2f94047e47929e9f283a20f0c817 |
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| Source note | uspto-grants-2016_02 |
|---|
