Boron tribromide → HCID 178517662, compound

HRID 1860553Notes

Reaction equation

HRID 1860553 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[C:4]([Cl:9])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][C:24](OC)=[C:23]([O:29]C)[CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([C:31]([F:34])([F:33])[F:32])[NH:11]1.B(Br)(Br)Br>C(Cl)Cl>[Cl:9][C:4]1[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[C:3]=1[N:10]1[C:14]2=[N:15][C:16]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([OH:29])[CH:22]=3)=[N:17][C:18](=[O:19])[C:13]2=[C:12]([C:31]([F:33])([F:32])[F:34])[NH:11]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 178489875HCID 178489875, compound

Product 1

HCID 178517662HCID 178517662, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 60 mg (0.12 mmol) of 1-(2,4,6-trichlorophenyl)-3-trifluoromethyl-6-(3-methoxy-4-methoxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one in 2 mL of CH2Cl2 was added 2 mL of a 1M solution of BBr3 in CH2Cl2. The solution was stirred 2.5 h at RT and quenched with 1 N aq. HCl. The mixture was diluted with water and extracted with EtOAc. The organic extract was washed with brine, dried (MgSO4), and concentrated under reduced pressure. The crude product was chromatographed on silica gel (elution with 1:1 hexanes-THF, then THF) to afford 1-(2,4,6-trichlorophenyl)-3-trifluoromethyl-6-(3-hydroxybenzyl)pyrazolo[3,4-d]pyrimidin-4-one, as an off-white solid. Mass spec.: 487 (M−H)−.

Workup

  1. customquenched with 1 N aq. HCl
  2. additionThe mixture was diluted with water
  3. extractionextracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was chromatographed on silica gel (
  9. washelution with 1:1 hexanes-THF

Sources & evidence

ORD record
ord-0742b5e5ea594fa2ae8c8f6b3771f1ac
Source dataset
uspto-grants-2003_03
Patent number
US06531477B1

Reaction notes

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