Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1H-Indole-4-boronic acid, pinacol ester | HCID 11322471 | — |
| Reactant | HCID 58268025 | HCID 58268025 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 44540690 | HCID 44540690 | 45.2% |
Reaction Steps
N-(6-Bromo-1-ethyl-1H-indazol-4-yl)-6-methyl-2-pyridinecarboxamide (50 mg, 0.14 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (available from Frontier Scientific, 38 mg, 0.17 mmol), Pd(dppf)Cl2 (23 mg), aqueous sodium carbonate (2M, 0.272 ml) and 1,4-dioxane (2 ml) were combined and heated at 150° C. for 10 mins under microwave conditions. The reaction was extracted into DCM (2×20 ml) and the combined organic layers were evaporated to dryness, before purification by Mass Directed Automated Preparative HPLC (Method B). Pure fractions were evaporated to give the title compound (25 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08765743B2 |
|---|
| Source dataset | uspto-grants-2014_07 |
|---|
| ORD ID | ord-8afcf81c800b4dc8b2bbb2a744e9423d |
|---|
| Source note | uspto-grants-2014_07 |
|---|
