Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 3-Methoxypropyne | HCID 69393 | — |
| Reactant | 5-bromo-3-iodo-1-methyl-1H-indazole | HCID 23156226 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | HCID 23156218 | HCID 23156218 | — |
Reaction Steps
A solution of 81.67 g of 5-bromo-3-iodo-1-methyl-1H-indazole in 750 ml of N,N-dimethylformamide and 335 ml of triethylamine is admixed at room temperature under argon with 25 ml of 3-methoxypropyne, 5.5 g of copper(I) iodide and 10 g of bis(triphenylphosphine)-palladium(II) chloride, and subsequently heated to 60° C. After 1 hour, the reaction mixture is cooled to room temperature, diluted with water and extracted with ethyl acetate (4×). The combined organic phases are dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellow solid from the residue by means of flash chromatography (SiO2 60 F). Rf=0.67 (2:1 EtOAc-heptane). Rt=4.42 (gradient I).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07851634B2 |
|---|
| Source dataset | uspto-grants-2010_12 |
|---|
| ORD ID | ord-ada65f1b50474e928f1e0d2e3f9d7960 |
|---|
| Source note | uspto-grants-2010_12 |
|---|
