HuagongsheHuagongshe Chemistry Print Report · For research reference only
Lithium Hydroxide → (1-(5-(2-Fluoro-5-methylphenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Lithium Hydroxide | HCID 3939 | — |
| Reactant | Pyrrolidine | HCID 31268 | — |
| Reactant | m-Chloroperbenzoic acid | HCID 70297 | — |
| Reactant | Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) | HCID 9886157 | — |
| Reactant | 2-Fluoro-5-methylbenzeneboronic acid | HCID 10351884 | — |
| Reactant | Methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate | HCID 118666039 | — |
| Product | (1-(5-(2-Fluoro-5-methylphenyl)pyrimidin-2-yl)-3-(methylsulfinyl)-1H-indol-6-yl)(pyrrolidin-1-yl)methanone | HCID 118666234 | — |
Reaction Steps
The synthesis example was prepared from methyl 1-(5-bromopyrimidin-2-yl)-3-(methylthio)-1H-indole-6-carboxylate in four chemical steps comprising a Suzuki reaction with (2-fluoro-5-methylphenyl)boronic acid, an oxidation with m-chloroperoxybenzoic acid, a hydrolysis of the methyl ester under use of lithium hydroxide and finally an amidation with HATU as coupling reagent and pyrrolidine as amine. White solid. Yield: 0.08 g
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09315490B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-f64d2dcaacc344c191a72ee4dfa9485d |
| Source note | uspto-grants-2016_04 |