HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → 3-(Benzofuran-5-yl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Benzofuran, 5-bromo- | HCID 90015 | — |
| Reactant | 3-Pyridinylboronic acid | HCID 2734378 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | 3-(Benzofuran-5-yl)pyridine | HCID 59595931 | 63.7% |
Reaction Steps
A solution of 5 pyridin-3-ylboronic acid (390 mg, 3.18 mmol), 5-bromobenzofuran (500 mg, 2.54 mmol), palladiumdichlorobis(triphenylphosphine) (111 mg, 0.16 mmol) and triethylamine (8.8 mL, 63.5 mmol) in EtOH was irradiated in the microwave at 100° C. for 1200 s. Removal of the solvents followed by dissolving in CH2Cl2 and filtering gave the residue after concentration of the solvent under reduced pressure. The compound was purifided on ISCO to afford 316 mg of the title compound as a light yellow solid: 1H NMR (400 MHz, CDCl3) δ 8.89 (s, 1H), 8.60 (d, 1H), 7.90 (d, 1H), 7.80 (s, 1H), 7.69 (s, 1H), 7.55 (d, 1H), 7.50 (d, 1H) 7.38 (dd, 1H), 6.85 (dd, 1H). MS (ESI) m/z: Calculated: 195.07; Observed: 196.30 (M++1).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07919519B2 |
| Source dataset | uspto-grants-2011_04 |
| ORD ID | ord-b16108105739491799c6639dfc2542c1 |
| Source note | uspto-grants-2011_04 |