Boron tribromide → HCID 59436002, compound

HRID 1802503Notes

Reaction equation

HRID 1802503 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:27])[C:9]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][N:23]=[C:24]([O:25]C)[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1)[C:5]#[N:6].B(Br)(Br)Br>C(Cl)(Cl)Cl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([Cl:27])[C:9]=1[NH:10][C:11]1[C:20]2[CH:21]=[CH:22][NH:23][C:24](=[O:25])[C:19]=2[C:18]2[C:13](=[CH:14][CH:15]=[N:16][CH:17]=2)[N:12]=1)[C:5]#[N:6]

Participants

5

Reactant 2

HCID 25134Boron tribromideHCID 59436081HCID 59436081, compound

Product 1

HCID 59436002HCID 59436002, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To a solution of 3,5-dichloro-4-[(10-methoxypyrido[4,3-c]-1,6-naphthyridin-6-yl)amino]benzonitrile (140 mg, 0.35 mmol) in chloroform (3 mL) was added boron tribromide (2.5 mL, 2.5 mmol, 1M in dichloromethane) and the mixture was heated at 85° C. for 45 min in a sealed tube. After cooling to room temperature, the reaction was diluted with ethyl acetate and washed 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 MeOH in dichloromethane to afford the title compound.

Workup

  1. temperatureAfter cooling to room temperature
  2. washwashed 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 MeOH in dichloromethane

Sources & evidence

ORD record
ord-65324205b5bb4a279c11c08e45f26dbd
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

Loading…