Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triphenylphosphine | HCID 11776 | — |
| Reactant | Diisopropyl diazene-1,2-dicarboxylate | HCID 75555 | — |
| Reactant | HCID 18466641 | HCID 18466641 | — |
| Reactant | quinolin-4-ol | HCID 178516385 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | HCID 3010647 | HCID 3010647 | 30% |
Reaction Steps
Diisopropyl azodicarboxylate (DIAD) (167 μL, 0.85 mmol) was added drop-wise to a solution of 11-(cyclopropyl)-5,11-dihydro-8-(2-hydroxyethyl)-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (175 mg, 0.57 mmol), 4-hydroxyquinoline (123 mg, 0.85 mmol) and Ph3P (223 mg, 0.85 mmol) in THF (2.8 mL) at room temperature. The mixture was stirred at room temperature for 3 h then was concentrated under reduced pressure. The residue was dissolved in EtOAc (60 mL) and the solution was successively washed with 3 N aqueous NaOH (3×20 mL), aqueous saturated NH4Cl (20 mL) and brine (20 mL) then was dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (EtOAc:MeOH; 95:5) to give the title compound (74 mg, 30% yield) as a white solid: MS (ESI) m/z 438 (MH)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US06420359B1 |
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| Source dataset | uspto-grants-2002_07 |
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| ORD ID | ord-376cba0db54e4278a5380c6e6486a880 |
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| Source note | uspto-grants-2002_07 |
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