Sodium Iodide → HCID 23130312, compound

HRID 2114174Notes

Reaction equation

HRID 2114174 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([C:18]2[C:19]([C:24]3[CH:29]=[CH:28][C:27]([C:30]([F:33])([F:32])[F:31])=[CH:26][CH:25]=3)=[CH:20][CH:21]=[CH:22][CH:23]=2)=[O:17])=[C:11]([N:34]([C:38](=[O:41])[CH2:39]Cl)[CH:35]([CH3:37])[CH3:36])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C=O)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:12]([N:15]([C:16]([C:18]3[C:19]([C:24]4[CH:25]=[CH:26][C:27]([C:30]([F:31])([F:32])[F:33])=[CH:28][CH:29]=4)=[CH:20][CH:21]=[CH:22][CH:23]=3)=[O:17])[CH2:39][C:38](=[O:41])[N:34]2[CH:35]([CH3:36])[CH3:37])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 5238Sodium IodideHCID 11430Potassium CarbonateHCID 58706380HCID 58706380, compound

Product 1

HCID 23130312HCID 23130312, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4′-trifluoromethylbiphenyl-2-carboxylic acid {4-benzyloxy-2-[(2-chloroacetyl)isopropylamino]phenyl}amide (134 mg) in DMF (2 mL) were added potassium carbonate (48 mg) and sodium iodide (one spatula), and he mixture was stirred at 80° C. for 2 hours. The reaction solution was allowed to stand for cooling to room temperature, and diluted with ethyl acetate. The extract was washed with water and saturated brine, dried over sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1) to give 7-benzyloxy-1-isopropyl-4-(4′-trifluoromethylbiphenyl-2-carbonyl)-3,4-dihydro-1H-quinoxalin-2-one (118 mg).

Workup

  1. temperaturefor cooling to room temperature
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-15915012e96b4c318ad6fbc055762b96
Source dataset
uspto-grants-2008_10
Patent number
US07432392B2

Reaction notes

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