Potassium Carbonate → HCID 16073189, compound

HRID 915513Notes

Reaction equation

HRID 915513 reaction equation
[C:1](=[O:4])([O-])[O-:2].[K+].[K+].[CH3:7][NH:8][C:9]([C:11]1[C:15]2[CH:16]=[C:17]([O:26][CH2:27][CH3:28])[C:18]([N:20]([S:22]([CH3:25])(=[O:24])=[O:23])[CH3:21])=[CH:19][C:14]=2[O:13][C:12]=1[C:29]1[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=1)=[O:10]>C(#N)C>[F:35][C:32]1[CH:33]=[CH:34][C:29]([C:12]2[O:13][C:14]3[CH:19]=[C:18]([N:20]([S:22]([CH3:25])(=[O:24])=[O:23])[CH3:21])[C:17]([O:26][CH2:27][C:28]4[CH:14]=[CH:15][C:11]([C:1]([OH:2])=[O:4])=[C:12]([OH:13])[CH:29]=4)=[CH:16][C:15]=3[C:11]=2[C:9](=[O:10])[NH:8][CH3:7])=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 16073188HCID 16073188, compound

Product 1

HCID 16073189HCID 16073189, compoundYield 192.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Preparation of compound 39(c) (5-(2,2-dimethyl-4-oxo-4H-benzo[1,3]dioxin-7-ylmethoxy)-2-(4-fluoro-phenyl)-6-(methanesulfonyl-methyl-amino)-benzofuran-3-carboxylic acid methylamide). Potassium carbonate (0.19 g, 1.38 mmol) and compound 39(b) (0.25 g, 0.917 mmol) were added to a solution of compound 38(d) (0.18 g, 0.459 mmol, which can be prepared according to Example 38 step d above), in acetonitrile (15 mL). The reaction mixture was refluxed for 4 hours and then concentrated in vacuo. The crude product was dissolved in ethyl acetate and washed with water. The organic layer was concentrated to a solid, which was triturated in 20% ethyl acetate/hexanes, filtered, and dried to provide 240 mg (90%) of the desired product as an off-white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 4 hours
  2. concentrationconcentrated in vacuo
  3. dissolutionThe crude product was dissolved in ethyl acetate
  4. washwashed with water
  5. concentrationThe organic layer was concentrated to a solid, which
  6. customwas triturated in 20% ethyl acetate/hexanes
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-76c3eca08144424c9eec668d6bfa28c1
Source dataset
uspto-grants-2007_09
Patent number
US07265152B2

Reaction notes

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