HuagongsheHuagongshe Chemistry Print Report · For research reference only
Ethyl Acetate → HCID 69027424, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Triacetoxyborohydride | HCID 2724942 | — |
| Reactant | 4-(5-Chlorothiophen-2-yl)benzaldehyde | HCID 53426317 | — |
| Reactant | 2-(2-Oxo-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester | HCID 54427836 | — |
| Catalyst | Acetic Acid | HCID 176 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 69027424 | HCID 69027424 | 56.7% |
Reaction Steps
To a solution of 2-(2-oxo-piperazin-1-ylmethyl)-pyrrolo[3,2-c]pyridine-1-carboxylic acid tert-butyl ester (0.10 g, 0.30 mmol) in acetonitrile (5 mL) is added 4-(5-chloro-thiophen-2-yl)-benzaldehyde (0.067 g, 0.30 mmol) followed by triacetoxyborohydride (0.13 g, 0.60 mmol) and glacial acetic acid (1 drop). The resulting mixture is stirred at room temperature overnight then poured into EtOAc and washed with water (×2) and brine. The organic layer is dried over MgSO4, filtered and concentrated to dryness then purified by column chromatography using EtOAc as the eluent to yield the title compound (0.90 g, 0.17 mmol). ESI MS [M+H]+=537.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07612075B2 |
| Source dataset | uspto-grants-2009_11 |
| ORD ID | ord-d7bee4c504c54b719c4e460c22562ef8 |
| Source note | uspto-grants-2009_11 |