Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Methanol | HCID 887 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | [2-(4-Bromo-2,5-dichloro-phenoxy)-pyridin-3-yl]-(4-cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)-methanone | HCID 59294468 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Product | HCID 59294520 | HCID 59294520 | 52% |
Reaction Steps
To a solution of [2-(4-bromo-2,5-dichloro-phenoxy)-pyridin-3-yl]-(4-cyclopropyl-3,4-dihydro-2H-quinoxalin-1-yl)-methanone (100 mg, 0.19 mmol, 1.0 equiv; Example 163) in a 1:1 mixture of methanol and ethyl acetate (4 mL) was added 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (10.1 mg, 0.012 mmol, 0.064 equiv; [CAS RN 95464-05-4]) and the reaction mixture stirred under an atmosphere of carbon monoxide (70 bar) at 100° C. for 20 h. The crude reaction mixture was filtered over Celite® and purified by silica column chromatography using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of heptane/ethyl acetate to afford 50 mg (52%) of the title compound as a off-white solid. MS (ISN): 498.3 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08309734B2 |
|---|
| Source dataset | uspto-grants-2012_11 |
|---|
| ORD ID | ord-814b250265fb4a5b8fb01ebbf0e5531d |
|---|
| Source note | uspto-grants-2012_11 |
|---|
