Boron tribromide → HCID 67060841, compound

HRID 1186095Notes

Reaction equation

HRID 1186095 reaction equation
[Cl:1][C:2]1[CH:32]=[C:31]([O:33]C)[C:5]2[NH:6][C:7](=[O:30])[CH:8]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[N:9]=[C:10]([C:11]3[CH:21]=[CH:20][C:14]4[NH:15][C:16](=[O:19])[N:17]([CH3:18])[C:13]=4[CH:12]=3)[C:4]=2[CH:3]=1.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:32]=[C:31]([OH:33])[C:5]2[NH:6][C:7](=[O:30])[CH:8]([CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=3[Cl:29])[N:9]=[C:10]([C:11]3[CH:21]=[CH:20][C:14]4[NH:15][C:16](=[O:19])[N:17]([CH3:18])[C:13]=4[CH:12]=3)[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 67060869HCID 67060869, compound

Product 1

HCID 67060841HCID 67060841, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 7-chloro-3-(2-chlorobenzyl)-9-methoxy-5-(3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one (25 mg, 0.05 mmol) under a nitrogen atmosphere was added 1M boron tribromide solution in dichloromethane (3 mL). This mixture was stirred at ambient temperature for 1 hour, then quenched with water (30 mL). Ethyl acetate (30 mL) was added and the mixture was slurried overnight. The layers were separated and the organic layer was dried with sodium sulfate, filtered and concentrated in vacuo. The product was purified by column chromatography eluting with a gradient of 0-20% methanol in dichloromethane to yield 7-chloro-3-(2-chlorobenzyl)-9-hydroxy-5-(3-methyl-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-5-yl)-1H-benzo[e][1,4]diazepin-2(3H)-one. HRMS [M+H]+ predicted: 481.0834. found: 481.0828.

Workup

  1. customquenched with water (30 mL)
  2. additionEthyl acetate (30 mL) was added
  3. waitthe mixture was slurried overnight
  4. customThe layers were separated
  5. dry with materialthe organic layer was dried with sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe product was purified by column chromatography
  9. washeluting with a gradient of 0-20% methanol in dichloromethane

Sources & evidence

ORD record
ord-b0229ab5d38440be8502f5d4c3a75038
Source dataset
uspto-grants-2014_03
Patent number
US08673897B2

Reaction notes

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