Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | HCID 59436011 | HCID 59436011 | — |
| Solvent | 1,1-Dichloroethane | HCID 6365 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 59435999 | HCID 59435999 | — |
Reaction Steps
To a slurry of 9-bromo-N-[2,6-dichloro-4-(1H-pyrazol-5-yl)phenyl]-1-methoxybenzo[c]-2,6-naphthyridin-5-amine (800 mg, 1.55 mmol) in dichloroethane (15 mL) was added boron tribromide (10.9 mL, 10.87 mmol, 1M in dichloromethane). The reaction mixture was heated at 85° C. for 45 min. After cooling to room temperature, the reaction was diluted with ethyl acetate and extracted with saturated aqueous sodium bicarbonate, followed by brine. The organic layer was dried with sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with THF in hexanes (0-50%) to afford the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08349865B2 |
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| Source dataset | uspto-grants-2013_01 |
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| ORD ID | ord-74d7b7c65365456691addbdd089461f0 |
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| Source note | uspto-grants-2013_01 |
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