HuagongsheHuagongshe Chemistry Print Report · For research reference only
1-Ethynylcyclopentanol → 7-chloro-4,5-dihydro-3-[(1-hydroxycyclopentyl)ethynyl]-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 1-Ethynylcyclopentanol | HCID 87074 | — |
| Reactant | 7-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one | HCID 19830659 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Diethylamine | HCID 8021 | — |
| Product | 7-chloro-4,5-dihydro-3-[(1-hydroxycyclopentyl)ethynyl]-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one | HCID 19851527 | — |
Reaction Steps
9.57 g (25.5 mmol) of 7-chloro-4,5-dihydro-3-iodo-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one was heated to boiling under reflux for 3 hours with 3.52 g (32 mmol) of 1-ethynylcyclopentanol, 170 mg of bis-(triphenylphosphine)-palladium(II) dichloride and 30 mg of copper(I) iodide in 60 ml of diethylamine. The reaction mixture was evaporated and the residue was chromatographed on silica gel while eluting with ethyl acetate. After crystallization from ethyl acetate there was obtained 7-chloro-4,5-dihydro-3-[(1-hydroxycyclopentyl)ethynyl]-5-methyl-6H-imidazo[1,5-a][1,4]benzodiazepin-6-one of melting point 207°-208°.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04863920 |
| Source dataset | uspto-grants-1989_09 |
| ORD ID | ord-03c7d4ea37454834801d325701f3d1b2 |
| Source note | uspto-grants-1989_09 |