Bromine → HCID 57897912, compound

HRID 1693538Notes

Reaction equation

HRID 1693538 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16](=[O:17])[C:15]3[N:14]=[CH:13][N:12]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[C:11]=3[N:10]=[C:9]2[C:24]2[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=2)=[CH:4][CH:3]=1.C([O-])(=O)C.[Na+].[Br:39]Br>C(O)(=O)C>[Br:39][C:13]1[N:12]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:11]2[N:10]=[C:9]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:31])[F:32])=[CH:26][CH:25]=3)[N:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)[C:16](=[O:17])[C:15]=2[N:14]=1

Participants

5

Reactant 3

HCID 24408BromineHCID 517045Sodium AcetateHCID 57898116HCID 57898116, compound

Product 1

HCID 57897912HCID 57897912, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

1-(4-Chloro-phenyl)-9-phenyl-2-(4-trifluoromethyl-phenyl)-1,9-dihydro-purin-6-one (50.0 mg, 0.107 mmol) and sodium acetate (300 mg) are dissolved in 10 mL of acetic acid. 250 μLs of bromine is added and the reaction mixture is stirred for 3 h. After the volatile is evaporated, the residue is partitioned with DCM and water. The organic layer is collected and evaporated to dryness. The crude material is purified by column chromatography, yielding 78 mg (84%) of 8-Bromo-1-(4-chloro-phenyl)-9-phenyl-2-(4-trifluoromethyl-phenyl)-1,9-dihydro-purin-6-one. 1H NMR (DMSO, 400 MHz) δ 7.63 (m, 5H), 7.57 (d, 2H), 7.50 (d, 2H), 7.43 (d, 2H), 7.39 (d, 2H). HPLC-MS calculated for C24H13BrClF3N4O (M+H+) 545.0. Found 545.0.

Workup

  1. customAfter the volatile is evaporated
  2. customthe residue is partitioned with DCM and water
  3. customThe organic layer is collected
  4. customevaporated to dryness
  5. customThe crude material is purified by column chromatography

Sources & evidence

ORD record
ord-8cbf40d498fa41fda9ee7e65a504bd9f
Source dataset
uspto-grants-2012_04
Patent number
US08158634B2

Reaction notes

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