Boron tribromide → HCID 135839338, compound

HRID 899321Notes

Reaction equation

HRID 899321 reaction equation
B(Br)(Br)Br.[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[C:27]([C:28]2[CH:33]=[CH:32][C:31]([O:34]C)=[CH:30][CH:29]=2)=[C:15]2[N:16]=[C:17]([CH3:26])[N:18]([CH2:21][C:22]([F:25])([F:24])[F:23])[C:19](=[O:20])[C:14]2=[N:13]1>C(Cl)Cl>[Cl:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N:12]1[C:27]([C:28]2[CH:29]=[CH:30][C:31]([OH:34])=[CH:32][CH:33]=2)=[C:15]2[N:16]=[C:17]([CH3:26])[N:18]([CH2:21][C:22]([F:25])([F:23])[F:24])[C:19](=[O:20])[C:14]2=[N:13]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 21880587HCID 21880587, compound

Product 1

HCID 135839338HCID 135839338, compoundYield 66.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

BBr3 (3 ml, 1 M solution in CH2Cl2) was added to a solution of 2-(2-chlorophenyl)-3-(4-methoxyphenyl)-5-methyl-6-(2,2,2-trifluoroethyl )-2,6-dihydropyrazolo[4,3-d]pyrimidin-7-one (4A-11, 545 mg, 1.21 mmol) in CH2Cl2 (20 ml) at room temperature. The reaction mixture was stirred for 2.5 h, quenched with MeOH (2 ml), and concentrated under vacuum. The residue was redissolved in MeOH (2 ml) and heated under reflux for 0.8 h, cooled to room temperature, and concentrated under vacuum. The residue was purified on a Chromatotron using 4 mm plates and 50% EtOAc/hexanes to give an impure mixture of the desired product (352 mg). A second purification on a Chromatotron using 1 mm plates and 50% EtOAc/hexanes yielded the desired product 6A-1 (55 mg) as an oil: MS (m/z) 435.4 (M+H)+; 1H NMR (400 MHz, CDCl3): δ 7.63-7.53 (m, 5H), 7.52-7.42 (m, 3H), 5.00-4.80 (br m, 2H), 2.66 (s, 3H).

Workup

  1. customquenched with MeOH (2 ml)
  2. concentrationconcentrated under vacuum
  3. dissolutionThe residue was redissolved in MeOH (2 ml)
  4. temperatureheated
  5. temperatureunder reflux for 0.8 h
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified on a Chromatotron
  8. customto give

Sources & evidence

ORD record
ord-a0949975416f4785bc7c8f818f365b33
Source dataset
uspto-grants-2008_04
Patent number
US07354929B2

Reaction notes

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