Boron tribromide dichloromethane → 5-(4-Hydroxyphenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione

HRID 1852505Notes

Reaction equation

HRID 1852505 reaction equation
C[O:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:15](=[O:16])[CH2:14][C:13](=[O:17])[NH:12][C:11]3[C:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=4[CH:24]=[CH:25][C:10]2=3)=[CH:5][CH:4]=1.B(Br)(Br)Br.ClCCl>ClCCl>[OH:2][C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:15](=[O:16])[CH2:14][C:13](=[O:17])[NH:12][C:11]3[C:18]4[CH2:19][CH2:20][CH2:21][CH2:22][C:23]=4[CH:24]=[CH:25][C:10]2=3)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 22277759Boron tribromide dichloromethaneHCID 866893235-(4-Methoxyphenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione

Product 1

HCID 866893225-(4-Hydroxyphenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dioneYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

5-(4-Methoxyphenyl)-1,5,8,9,10,11-hexahydronaphtho[1,2-b][1,4]diazepine-2,4-dione (200 mg, 0.59 mmol) obtained in Example 13 was dissolved in dry dichloromethane (5 mL) while stirring in ice-bath. To the solution was dropwise added 1M boron tribromide-dichloromethane (1.2 mL). The mixture was stirred at room temperature for 16 hours and at 50° C. for 3 hours. The solvent was removed by evaporation under reduced pressure. To the residue was added cold water. The mixture was extracted with ethyl acetate, washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was removed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=100/1) to give the titled compound as a white amorphous form (124 mg, yield 64%).

Workup

  1. stirringThe mixture was stirred at room temperature for 16 hours and at 50° C. for 3 hours
  2. customThe solvent was removed by evaporation under reduced pressure
  3. additionTo the residue was added cold water
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was removed by evaporation under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-67df5d5c561843ce8525ca7780aba44c
Source dataset
uspto-grants-2015_02
Patent number
US08962613B2

Reaction notes

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