Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| Reactant | HCID 89539133 | HCID 89539133 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | HCID 89539118 | HCID 89539118 | 80% |
Reaction Steps
The mixture of ethyl 4-bromo-2-isonicotinoylthiophene-3-carboxylate (325 mg, 0.96 mmol), 4-pyridineboronic acid (177 mg, 1.44 mmol), Na2CO3 (254 mg, 2.4 mmol) and PdCl2(dppf) (63 mg, 0.077 mmol) was dissolved in 12 mL dioxane/H2O (3:1). The mixture was stirred at 100° C. for 2 h. After completion of the reaction the resulting mixture was concentrated under reduced pressure. The material was loaded onto a silica gel column and eluted with 20%-50% EtOAc/PE. Elution fractions containing the desired compounds were collected and the solvent was removed under reduced pressure to provide the title compound (260 mg, 80% yield) as an orange oil. LC-MS (Method A): m/z 339 (M+H)+, Rt: 1.77 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09200005B2 |
|---|
| Source dataset | uspto-grants-2015_12 |
|---|
| ORD ID | ord-e215a69e980c4b669a9dacd76fae07cc |
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| Source note | uspto-grants-2015_12 |
|---|
