Imidazole → HCID 59864892, compound

HRID 2423291Notes

Reaction equation

HRID 2423291 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:23][C:24]([O:26][CH3:27])=[O:25])[CH:6]=[CH:7][C:8]=1[O:9][C:10]1[C:11]([N+:20]([O-:22])=[O:21])=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][C:14](=O)[CH2:13]2.P(Br)(Br)([Br:30])=O.N1C=CN=C1>ClCCCl>[Br:30][C:14]1[NH:15][C:16]2[C:12]([CH:13]=1)=[C:11]([N+:20]([O-:22])=[O:21])[C:10]([O:9][C:8]1[CH:7]=[CH:6][C:5]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:4][C:3]=1[O:2][CH3:1])=[CH:18][CH:17]=2

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24613Phosphorus oxybromideHCID 59864855HCID 59864855, compound

Product 1

HCID 59864892HCID 59864892, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of methyl 2-(3-methoxy-4-(4-nitro-2-oxoindolin-5-yloxy)phenyl)acetate (0.177 g, 0.476 mmol) in DCE (10 mL), phosphoryl tribromide (0.273 g, 0.952 mmol) was added dropwise at room temperature. The mixture was heated at 90° C. for 1 h, and then imidazole (0.049 g, 0.714 mmol) was added and heated for another 2 h. The reaction was quenched with ice, adjusted PH to 8 and diluted with ethyl acetate. The organic layer was washed with saturated brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. MS ESI (pos.) m/z: 435.1 (M+H)+

Workup

  1. temperatureheated for another 2 h
  2. customThe reaction was quenched with ice
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b8fdbcacf99e456785bfbe4468f4b2c0
Source dataset
uspto-grants-2011_06
Patent number
US07960567B2

Reaction notes

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