Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Water | HCID 962 | — |
| Reactant | Allyltributylstannane | HCID 90628 | — |
| Reactant | HCID 18466636 | HCID 18466636 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 18466623 | HCID 18466623 | 51% |
Reaction Steps
Allyltributyltin (7.77 mL, 25.1 mmol) and Pd(Ph3P)4 (1.32 g, 1.14 mmol) were added to a degassed (N2 through solution for 30 min) solution of 8-bromo-5,11-dihydro-11-ethyl-2-fluoro-4-methyl-6H-dipyrido[3,2-b:2′,3′-e][1,4]diazepin-6-one (8.0 g, 22.8 mmol) in DMF (114 mL). The mixture was heated to 90° C. for 3 h. The mixture was poured into water (250 mL) and extracted with EtOAc (4×250 mL). The combined organic layers were washed with 20% aqueous NH40H (250 mL) and brine (250 mL), dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (hexanes:EtOAc, 4:1 to 1:1) to give the title compound (3.16 g, 51% yield).
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-7dd0526967164bf5a33d5b9d78b93ee8 |
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| Source note | uspto-grants-2002_07 |
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