HuagongsheHuagongshe Chemistry Print Report · For research reference only
Trimethylamine → 5-((2-chloropyrimidin-4-yl)oxy)-2-methyl-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Trimethylamine | HCID 1146 | — |
| Reactant | Potassium Hydroxide | HCID 14797 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 2,4-Dichloropyrimidine | HCID 77531 | — |
| Reactant | Diisopropylethylamine | HCID 81531 | — |
| Reactant | 2-methyl-1H-indol-5-ol | HCID 83336 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Solvent | Pyridine | HCID 1049 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-((2-chloropyrimidin-4-yl)oxy)-2-methyl-1H-indole | HCID 59823359 | — |
Reaction Steps
The title compound 3 can be prepared by the reaction of 5-hydroxyl-2-methyl-indole (compound 1) with 2,4-dichloropyrimidine (compound 2) in the presence of a base, such as but not limited to NaHCO3, KOH, NaOH, K2CO2, KHCO3, diisopropylethylamine (DIPEA), pyridine, triethylamine (TEA) or trimethylamine; in a solvent, such as but not limited to acetonitrile, N,N-dimethylforamide (DMF), dioxane, tetrahydrofuran (THF). The reaction may be carried out at a suitable temperature, such as a temperature ranging from 0 to 60° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08658658B2 |
| Source dataset | uspto-grants-2014_02 |
| ORD ID | ord-4aa5c5a168eb4cdaad867aed6b1bf03a |
| Source note | uspto-grants-2014_02 |