HCID 22479239, compound → HCID 22479224, compound

HRID 2182626Notes

Reaction equation

HRID 2182626 reaction equation
[Br:1][C:2]1[CH:28]=[CH:27][C:5]([CH2:6][C:7]23[CH2:14][CH2:13][CH2:12][N:11]2[C:10](=[O:15])[N:9]([C:16]2[CH:21]=[C:20]([Cl:22])[C:19]([O:23]C)=[C:18]([Cl:25])[CH:17]=2)[C:8]3=[O:26])=[CH:4][CH:3]=1>Br>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][C:7]23[CH2:14][CH2:13][CH2:12][N:11]2[C:10](=[O:15])[N:9]([C:16]2[CH:21]=[C:20]([Cl:22])[C:19]([OH:23])=[C:18]([Cl:25])[CH:17]=2)[C:8]3=[O:26])=[CH:27][CH:28]=1

Participants

3

Reactant 1

HCID 22479239HCID 22479239, compound

Product 1

HCID 22479224HCID 22479224, compoundYield 83.7%

Reagents, catalysts & solvents 1

HCID 260Hydrogen BromideSolvent

Procedure

The compound from Example 134 (0.8 g) was taken in aqueous HBr (10 mL) and the solution was refluxed overnight. The aqueous solution was extracted with EtOAc. The combined organic layers were dried over Na2SO4, filtered and evaporated. The residue was purified by flash chromatography on silica gel (1:1 EtOAc/Hexanes) to yield the titled compound (0.65 g). MS (m/z) 469 (MH+).

Workup

  1. temperaturethe solution was refluxed overnight
  2. extractionThe aqueous solution was extracted with EtOAc
  3. dry with materialThe combined organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (1:1 EtOAc/Hexanes)

Sources & evidence

ORD record
ord-50c2f4f4331b40a0977b84dbfff6b679
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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