Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 5-Indolylboronic acid | HCID 2734361 | — |
| Reactant | 5-Bromo-3-pyridinecarboxaldehyde | HCID 2784734 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86616467 | HCID 86616467 | 62.6% |
Reaction Steps
Indole-5-boronic acid (1 g 6.25 mmol), 5-bromopyridine-3-carboxaldehyde (1.3 g, 6.9 mmol) and PdCl2(dppf).DCM (2.2 g, 2.7 mmol) and 15 ml of dioxane were evenly distributed amongst five 5 mL microwave vessels (Smith Personal Chemistry). The mixtures were degassed (evacuate in vacuo and pressurize with nitrogen). Sodium carbonate in water (2M, 9.38 mL, 18.7 mmol) was evenly distributed amongst the reaction vessels and the mixtures degassed two more times as described above. The mixture was heated to 100° C. for 12 min in a Smith synthesizer. The samples were cooled, combined and washed with water. The aqueous phase was extracted with dichloromethane and the combined organic phases were dried over MgSO4, filtered and evaporated to give crude product. Chromatography (elution with ethyl acetate/cyclohexane) provided 870 mg of product.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07625889B2 |
|---|
| Source dataset | uspto-grants-2009_12 |
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| ORD ID | ord-ab2325341edd46ab8fabefc734a8b9f3 |
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| Source note | uspto-grants-2009_12 |
|---|
