Boron tribromide → HCID 136082626, compound

HRID 1186098Notes

Reaction equation

HRID 1186098 reaction equation
[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[NH:6][C:7](=[O:29])[CH:8]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[Cl:28])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[C:13]([CH3:19])[CH:12]=3)[C:4]=2[CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:31]=[CH:30][C:5]2[NH:6][C:7](=[O:29])[CH:8]([CH2:20][C:21]3[CH:26]=[CH:25][C:24]([F:27])=[CH:23][C:22]=3[Cl:28])[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([CH3:19])[CH:12]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 70664321HCID 70664321, compound

Product 1

HCID 136082626HCID 136082626, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

7-Chloro-3-(2-chloro-4-fluorobenzyl)-5-(4-methoxy-3-methylphenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (0.158 g, 0.345 mmol) was dissolved in dichloromethane (DCM, 2 mL) and BBr3 in DCM (1 M, 1.73 mL, 1.73 mmol) was added dropwise. The mixture was stirred at room temperature for 4 h. then quenched with methanol and diluted with ethyl acetate. The organic solution was washed with saturated sodium bicarbonate (aq) then brine. It was concentrated onto silica gel then chromatographed on silica gel eluting with 35-40-45% ethyl acetate in hexanes to give 7-chloro-3-(2-chloro-4-fluorobenzyl)-5-(4-hydroxy-3-methylphenyl)-1H-benzo[e][1,4]diazepin-2(3H)-one as a yellow oil which precipitated as a pale yellow solid from chloroform (158 mg, 0.345 mmol).

Workup

  1. customthen quenched with methanol
  2. additiondiluted with ethyl acetate
  3. washThe organic solution was washed with saturated sodium bicarbonate (aq)
  4. concentrationIt was concentrated onto silica gel
  5. customthen chromatographed on silica gel eluting with 35-40-45% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-d0a6fd73a9f84f289fa9061fef9244e9
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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