Ethyl ketone → HCID 86595461, compound

HRID 1618146Notes

Reaction equation

HRID 1618146 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[F:20])[O:5][C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[C:11](=[O:15])[NH:10][C:9]2=[O:16].C(=O)([O-])[O-].[K+].[K+].CCC(=O)CC.Br[CH2:34][C:35]([O:37][CH3:38])=[O:36]>O>[CH3:38][O:37][C:35](=[O:36])[CH2:34][N:10]1[C:9](=[O:16])[C:8]2[C:12](=[CH:13][CH:14]=[C:6]([O:5][C:4]3[CH:17]=[CH:18][C:19]([F:20])=[C:2]([F:1])[CH:3]=3)[CH:7]=2)[C:11]1=[O:15]

Participants

6

Reactant 4

HCID 7288Ethyl ketoneHCID 11430Potassium CarbonateHCID 60984Methyl bromoacetateHCID 66712584HCID 66712584, compound

Product 1

HCID 86595461HCID 86595461, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
105 °C

Procedure

To a pressure tube was added 5-(3,4-difluoro-phenoxy)-isoindole-1,3-dione (680 mg), potassium carbonate (1 g), 3-pentanone (20 ml), and methyl bromoacetate (295 μL). The resulting mixture was heated to 105° C. for 17 h. The reaction was diluted with 20 ml water and extracted with ethyl acetate (2×). The organic layer was dried and concentrated. The mixture was purified through silica gel chromatography with 4:1 hexanes/ethyl acetate and 3:1 hexanes/ethyl acetate to give 657 mg title compound. 1H NMR (200 MHz, DMSO) δ 7.95 (d, J=9.0 Hz, 1H), 7.64-7.41 (m, 4H), 7.15-7.08 (m, 1H), 4.44 (s, 2H), 3.70 (s, 3H).

Workup

  1. extractionextracted with ethyl acetate (2×)
  2. customThe organic layer was dried
  3. concentrationconcentrated
  4. customThe mixture was purified through silica gel chromatography with 4:1 hexanes/ethyl acetate and 3:1 hexanes/ethyl acetate

Sources & evidence

ORD record
ord-6414222c192243288c2f8c13398b8a83
Source dataset
uspto-grants-2014_07
Patent number
US08765956B2

Reaction notes

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