Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | 3-Methoxypropyne | HCID 69393 | — |
| Reactant | Methyl 5-bromo-3-chloropyridine-2-carboxylate | HCID 46311201 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 71271169 | HCID 71271169 | — |
Reaction Steps
To a solution of 3-methoxy-propyne (421 mg, 6 mmol), bis(triphenylphosphine)palladium(II) chloride (84 mg, 0.12 mmol), copper(I) iodide (23 mg, 0.12 mmol) and N Eta (1.17 ml, 8.4 mmol) in THF (10 ml) under Argon was added 3-chloro-5-bromo-pyridine-2-carboxylic acid methyl ester (284 mg, 1.2 mmol) and the mixture was heated to 80° C. for 5 h. At 0° C. water (12 ml) was added and the mixture was extracted with EtOAc. The aq. Phase was acidified to pH 1 by addition of 1N HCl, extracted with DCM. The combined DCM extracts were washed with half-saturated aq. sodium chloride, dried with Na2SO4 and evaporated to provide the title compound as an off-white solid, which was used for coupling reactions without further purification.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US09163011B2 |
|---|
| Source dataset | uspto-grants-2015_10 |
|---|
| ORD ID | ord-c636506c24b544f7a3bbff736b54783d |
|---|
| Source note | uspto-grants-2015_10 |
|---|
