Boron tribromide → HCID 71255050, compound

HRID 540320Notes

Reaction equation

HRID 540320 reaction equation
[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:12]C)[CH:10]=2)[N:5]=[C:4]([N:14]2[CH2:20][CH2:19][CH2:18][C:17]3[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=3[CH2:15]2)[CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([OH:12])[CH:10]=2)[N:5]=[C:4]([N:14]2[CH2:20][CH2:19][CH2:18][C:17]3[CH:21]=[CH:22][CH:23]=[CH:24][C:16]=3[CH2:15]2)[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 71255212HCID 71255212, compound

Product 1

HCID 71255050HCID 71255050, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-chloro-6-methoxy-quinolin-2-yl)-2,3,4,5-tetrahydro-1H-2-benzazepine (800 mg, 2.37 mmol) in 15 mL of dichloromethane was added slowly a solution of boron tribromide (0.558 mL, 5.9 mmol). The resulting mixture was stirred at room temperature for 30 minutes, followed by stirring at 40° C. for 2 hours. After cooled to room temperature, the reaction mixture was carefully quenched with sodium bicarbonate (20 mL), and then extracted with dichloromethane (10 mL×3). The organic layers were combined and washed with brine (20 ml), then dried over sodium sulfate. The solvent was removed in vacuo and the residue was purified by flash column chromatography on silica gel (ethyl acetate/hexane, 1:5) to give 500 mg of product (yield was 65%).

Workup

  1. stirringby stirring at 40° C. for 2 hours
  2. temperatureAfter cooled to room temperature
  3. customthe reaction mixture was carefully quenched with sodium bicarbonate (20 mL)
  4. extractionextracted with dichloromethane (10 mL×3)
  5. washwashed with brine (20 ml)
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed in vacuo
  8. customthe residue was purified by flash column chromatography on silica gel (ethyl acetate/hexane, 1:5)

Sources & evidence

ORD record
ord-81706177a2154ec59390eb5ee1a6b348
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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