HuagongsheHuagongshe Chemistry Print Report · For research reference only
Water → 3-bromo-1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Water | HCID 962 | — |
| Reactant | trimethylsilyl N-trimethylsilylethanimidate | HCID 25248 | — |
| Reactant | N-bromobutanimide | HCID 67184 | — |
| Reactant | 1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one | HCID 117987824 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 3-bromo-1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one | HCID 117988493 | 69.4% |
Reaction Conditions
| Temperature | 40 °C |
|---|
Reaction Steps
To a solution of 1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one (3.40 g) in DMF (42.0 mL) was added trimethylsilyl N-(trimethylsilyl)ethanimidate (7.52 g) at room temperature, and the mixture was stirred at 40° C. for 3 hr. The reaction mixture was allowed to be cooled to room temperature, and NBS (3.59 g) was added thereto at room temperature. The reaction mixture was stirred overnight at room temperature, water was added thereto, and the mixture was stirred at room temperature for 2 hr. The white precipitate was collected by filtration, and dried under reduced pressure to give the title compound (3.28 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09371320B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-f96fa7a44c5d4f9cb7b5f2f9ff9ae4cd |
| Source note | uspto-grants-2016_06 |