Potassium Carbonate → HCID 89954963, compound

HRID 705382Notes

Reaction equation

HRID 705382 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([NH:21][S:22]([CH3:25])(=[O:24])=[O:23])[C:18]([O:26][CH:27]([CH3:29])[CH3:28])=[CH:17][C:11]=3[C:12]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:36][O:37][C:38]1[CH:45]=[CH:44][C:41]([CH2:42]Br)=[CH:40][CH:39]=1>CN(C)C=O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:20]=[C:19]([N:21]([CH2:42][C:41]4[CH:44]=[CH:45][C:38]([O:37][CH3:36])=[CH:39][CH:40]=4)[S:22]([CH3:25])(=[O:23])=[O:24])[C:18]([O:26][CH:27]([CH3:29])[CH3:28])=[CH:17][C:11]=3[C:12]=2[C:13]([O:15][CH3:16])=[O:14])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1650214-Methoxybenzyl bromideHCID 67210939HCID 67210939, compound

Product 1

HCID 89954963HCID 89954963, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

Methyl 2-(4-fluorophenyl)-5-isopropoxy-6-(methylsulfonamido)benzofuran-3-carboxylate (0.65 g, 1.5 mmol) was dissolved in 10 mL N,N-dimethylformamide and treated sequentially with potassium carbonate (0.26 g, 1.85 mmol) and 4-methoxybenzyl bromide (0.27 mL, 1.85 mmol). The slurry was stirred and heated at 70° C. for 3 hours. The reaction mixture was concentrated in vacuo to a pasty solid. The residue was dissolved in 100 mL ethyl acetate, washed with 1 N aqueous H3PO4 and 10% aqueous sodium chloride, dried over anhydrous sodium sulfate(s), filtered and the solvent was removed in vacuo leaving a yellow oil, 0.8 g.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo to a pasty solid
  2. dissolutionThe residue was dissolved in 100 mL ethyl acetate
  3. washwashed with 1 N aqueous H3PO4 and 10% aqueous sodium chloride
  4. dry with materialdried over anhydrous sodium sulfate(s)
  5. filtrationfiltered
  6. customthe solvent was removed in vacuo
  7. customleaving a yellow oil, 0.8 g

Sources & evidence

ORD record
ord-390f5b2efd7b4f47b6a6ef884d71c405
Source dataset
uspto-grants-2015_11
Patent number
US09173887B2

Reaction notes

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