Boron tribromide → HCID 136038186, compound

HRID 1189482Notes

Reaction equation

HRID 1189482 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([C:14]1[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=1)[N:20]1[C:24]([C:27]4[CH:32]=[CH:31][C:30]([O:33]C)=[CH:29][CH:28]=4)=[N:25][N:26]=[C:19]1[C:18](=[O:35])[NH:17]3)=[O:13])[CH2:7]2.B(Br)(Br)Br>ClCCl>[Cl:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([C:14]1[CH:15]=[C:16]3[C:21](=[CH:22][CH:23]=1)[N:20]1[C:24]([C:27]4[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=4)=[N:25][N:26]=[C:19]1[C:18](=[O:35])[NH:17]3)=[O:13])[CH2:7]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 58575331HCID 58575331, compound

Product 1

HCID 136038186HCID 136038186, compoundYield 4.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of 403 mg of 7-[(5-chloro-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]-1-(4-methoxyphenyl)[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one and 10 mL of dichloromethane was added 2.9 mL of a 1 M boron tribromide solution in dichloromethane, followed by stirring at the same temperature for 16 hours. The reaction liquid was poured into ice-water, followed by stirring for 5 minutes and extracting with chloroform. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate, and then the solvent was evaporated. The obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 97/3) and then further purified by preparative HPLC (acetonitrile/0.01% aqueous formic acid solution). The obtained solid was heated and washed with a mixed solvent of 3 mL of methanol and 1 mL of water to obtain 18 mg of 7-[(5-chloro-3,4-dihydroisoquinolin-2(1H)-yl)carbonyl]-1-(4-hydroxyphenyl)[1,2,4]triazolo[4,3-a]quinoxalin-4(5H)-one as a white solid.

Workup

  1. customThe reaction liquid
  2. stirringby stirring for 5 minutes
  3. extractionextracting with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was evaporated
  7. customThe obtained residue was purified by silica gel column chromatography (chloroform/methanol=100/0 to 97/3)
  8. customfurther purified by preparative HPLC (acetonitrile/0.01% aqueous formic acid solution)
  9. temperatureThe obtained solid was heated
  10. washwashed with a mixed solvent of 3 mL of methanol and 1 mL of water

Sources & evidence

ORD record
ord-6108db35e706432787eebf0dfe655579
Source dataset
uspto-grants-2014_03
Patent number
US08674096B2

Reaction notes

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