Boron tribromide → HCID 59435999, compound

HRID 1802480Notes

Reaction equation

HRID 1802480 reaction equation
[Br:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]=[C:7]([NH:16][C:17]3[C:22]([Cl:23])=[CH:21][C:20]([C:24]4[NH:28][N:27]=[CH:26][CH:25]=4)=[CH:19][C:18]=3[Cl:29])[C:8]3[C:13]([C:4]=2[CH:3]=1)=[C:12]([O:14]C)[N:11]=[CH:10][CH:9]=3.B(Br)(Br)Br>ClC(Cl)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:31]=[CH:30][C:5]2[N:6]=[C:7]([NH:16][C:17]3[C:18]([Cl:29])=[CH:19][C:20]([C:24]4[NH:28][N:27]=[CH:26][CH:25]=4)=[CH:21][C:22]=3[Cl:23])[C:8]3[CH:9]=[CH:10][NH:11][C:12](=[O:14])[C:13]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 59436011HCID 59436011, compound

Product 1

HCID 59435999HCID 59435999, compound

Reagents, catalysts & solvents 2

HCID 63651,1-DichloroethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

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.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionextracted with saturated aqueous sodium bicarbonate
  3. dry with materialThe organic layer was dried with sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel eluting with THF in hexanes (0-50%)

Sources & evidence

ORD record
ord-74d7b7c65365456691addbdd089461f0
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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