Hydrochloric Acid → HCID 66709746, compound

HRID 1193036Notes

Reaction equation

HRID 1193036 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:17](=[O:18])[CH:16]3[CH:11]([CH:12]4[CH2:20][CH2:19][CH:15]3[CH2:14][CH2:13]4)[C:10]2=[O:21])=[C:4]([CH3:22])[CH:3]=1.[Cl:23][C:24]1[CH:25]=[C:26]([F:31])[C:27](F)=[N:28][CH:29]=1.C(=O)([O-])[O-].[K+].[K+].Cl>>[Cl:23][C:24]1[CH:25]=[C:26]([F:31])[C:27]([O:1][C:2]2[CH:3]=[C:4]([CH3:22])[C:5]([CH:9]3[C:10](=[O:21])[CH:11]4[CH:16]([CH:15]5[CH2:19][CH2:20][CH:12]4[CH2:13][CH2:14]5)[C:17]3=[O:18])=[C:6]([CH3:8])[CH:7]=2)=[N:28][CH:29]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 27832485-Chloro-2,3-difluoropyridineHCID 66709744HCID 66709744, compound

Product 1

HCID 66709746HCID 66709746, compound

Conditions

Temperature
140 °C

Procedure

To a mixture of 2-(4-hydroxy-2,6-dimethylphenyl)hexahydro-4,7-ethanoindene-1,3-dione (0.40 g, 0.0013 mol), 5-chloro-2,3-difluoropyridine (0.20 g, 0.0013 mol) and potassium carbonate (0.40 g, 0.0029 mol) is added N,N-dimethylaminopyridine (10 ml), and the reaction mixture is then heated at 140° C. for 40 minutes under microwave irradiation. After cooling to room temperature 2M aqueous hydrochloric acid is added, and the crude product is extracted with ethyl acetate. The organic phase is separated, washed with distilled water, then dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is then purified by preparative reverse phase HPLC to afford 2-[4-(5-chloro-3-fluoropyridin-2-yloxy)-2,6-dimethylphenyl]hexahydro-4,7-ethanoindene-1,3-dione as a cream solid.

Workup

  1. additionis added
  2. extractionthe crude product is extracted with ethyl acetate
  3. customThe organic phase is separated
  4. washwashed with distilled water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is then purified by preparative reverse phase HPLC

Sources & evidence

ORD record
ord-e065364db85745a29aff6c9151158083
Source dataset
uspto-grants-2014_03
Patent number
US08680339B2

Reaction notes

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