HuagongsheHuagongshe Chemistry Print Report · For research reference only
Benzodiazepine → N-methylbenzodiazepine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Benzodiazepine | HCID 134664 | — |
| Reactant | Methyl iodide sodium hydride | HCID 23686416 | — |
| Product | N-methylbenzodiazepine | HCID 12543525 | — |
Reaction Steps
The bromide 20 (Bogatskii A V, et al., (1977) Pharm Chem J (Engl Transl) 11:1520-1525; Vejdelek Z, Protiva M (1983) Collect Czech Chem Commun 48:1477-1482) was reacted with trimethylsilyacetylene in the presence of a palladium catalyst to provide trimethylsilyl analog 52. This product was methylated with methyl iodide/sodium hydride to give the N-methyl benzodiazepine 54 (XLi 351). This was subjected to fluoride-mediated desilylation to furnish 53 (XLi 350) from 53 and 55 (XLi 352) from 54.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07618958B2 |
| Source dataset | uspto-grants-2009_11 |
| ORD ID | ord-fff88c841036420e8710bf6cfacda0a0 |
| Source note | uspto-grants-2009_11 |