Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 6-Bromopyridine-2-carbaldehyde | HCID 2757009 | — |
| Reactant | 12152-94-2 | HCID 15398362 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Product | HCID 178519542 | HCID 178519542 | — |
Reaction Steps
See Scheme 1. Toluene (500 mL) was added to a mixture of 2-bromo-6-pyridinecarboxaldehyde (16.25 g, 87.36 mmol, purchased from Sigma-Aldrich), ferrocenylboronic acid (24.10 g, 104.9 mmol, purchased from Sigma-Aldrich), and (dppf)PdCl2.CH2Cl2 (2.14 g, 2.62 mmol, purchased from Strem), under a nitrogen atmosphere. Then a nitrogen-sparged solution of Na2CO3 (210 mL, 210 mmol) in 4:1 water:methanol was added. The biphasic mixture was heated to 60° C. After 1 hour, the solution was heated to 80° C. for one week. The mixture was then filtered and the organics were separated and dried over MgSO4. Evaporation yielded the crude 6-ferrocenyl-2-pyridinecarboxaldehyde which was purified on SiO2 using 3:1 to 4:1 CH2Cl2:hexane as the elutant. Yield: 6.02 g, 23.7%. 1H NMR (C6D6): δ 10.18 (1H, s), 7.58 (1H, d), 8.03-6.85 (2H, m), 4.91 (2H, m), 4.20 (2H, m), 3.86 (5H, s).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07858817B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-dcf33cad366d4f36a32a9a67ff87d7a7 |
|---|
| Source note | uspto-grants-2010_12 |
|---|
