Boron tribromide → HCID 117699273, compound

HRID 1049694Notes

Reaction equation

HRID 1049694 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16]([N:19]2[C:25](=[O:26])[CH2:24][C:23](=[O:27])[NH:22][C:21]3[C:28]4[C:33]([CH:34]=[CH:35][C:20]2=3)=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:15][CH:14]=1)=[O:11].B(Br)(Br)Br>ClCCl>[OH:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C:10]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([N:19]2[C:25](=[O:26])[CH2:24][C:23](=[O:27])[NH:22][C:21]3[C:28]4[C:33]([CH:34]=[CH:35][C:20]2=3)=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:17][CH:18]=1)=[O:11]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 117699105HCID 117699105, compound

Product 1

HCID 117699273HCID 117699273, compoundYield 28.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-[4-[(2-Methoxyphenylacetyl)amino]phenyl]-1H-naphtho[1,2-b][1,4]diazepine-2,4(3H,5H)-dione (50 mg, 0.11 mmol) obtained in Example 22 was dissolved in dry dichloromethane (20 mL), the solution was added with a 1 M solution of boron tribromide in dichloromethane (0.22 mL), and the mixture was stirred at room temperature for 24 hours. The solvent was evaporated, the residue was added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate to give the title compound (14 mg, yield 28%) as pale yellow crystals.

Workup

  1. customThe solvent was evaporated
  2. additionthe residue was added with saturated aqueous sodium hydrogencarbonate
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. washthe residue was washed with ethyl acetate

Sources & evidence

ORD record
ord-8c56dbb7931146b2a5fe85bb8ad6269f
Source dataset
uspto-grants-2016_07
Patent number
US09382236B2

Reaction notes

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