Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Tributylamine | HCID 7622 | — |
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | 1-Hexyne | HCID 12732 | — |
| Reactant | HCID 22387948 | HCID 22387948 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 22388280 | HCID 22388280 | 69.5% |
Reaction Steps
A mixture of methyl 3-(2-chloro-4-iodobenzyl)-2-methyl-3H-imidazo[4,5-b]pyridine-5-carboxylate (2.31 g), 1-hexyne (2.00 g), palladium(II) acetate (235 mg), triphenylphosphine (549 mg), copper(I) iodide (297 mg), tributylamine (2.91 g) and dimethylformamide (23 ml) was stirred under an nitrogen atmosphere at 60° C. for 1.5 hr. The reaction mixture was partitioned between ethyl acetate and water. The organic layer was washed with water, dried and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1-1:2) to give the objective compound (1.44 g) as a gray powder.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06911469B2 |
|---|
| Source dataset | uspto-grants-2005_06 |
|---|
| ORD ID | ord-0206ba3fc78a423095641a6c5a5a80eb |
|---|
| Source note | uspto-grants-2005_06 |
|---|
