Potassium Hydroxide → HCID 67508560, compound

HRID 1400025Notes

Reaction equation

HRID 1400025 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[OH-].[K+].[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[C:17](=[O:22])[NH:18][C:19](=[O:21])[CH:20]=2)=[C:12]([F:23])[CH:11]=1>CS(C)=O>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]23[CH2:2][CH:20]2[C:19](=[O:21])[NH:18][C:17]3=[O:22])=[C:12]([F:23])[CH:11]=1

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 67508406HCID 67508406, compound

Product 1

HCID 67508560HCID 67508560, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of trimethylsulfoxonium iodide (3.18 g, 14.5 mmol) in DMSO (15 mL) was added KOH (1.08 g, 19.3 mmol) at r.t. The reaction mixture was stirred at r.t. for 30 min followed by addition of 3-(4-bromo-2-fluoro-phenyl)-pyrrole-2,5-dione (2.60 g, 9.6 mmol). The reaction mixture was stirred at r.t. and progress of the reaction was monitored by TLC. On completion, the reaction mixture was quenched with saturated NH4Cl (10 mL) and extracted with ethyl acetate (2×20 mL). The organic layer was washed with brine (10 mL), dried over anhydrous sodium sulphate and concentrated in vacuo. The title compound was obtained as brown solid in crude form (2.51 g, 92%) and was as such used in the next step.

Workup

  1. stirringThe reaction mixture was stirred at r.t.
  2. customOn completion, the reaction mixture was quenched with saturated NH4Cl (10 mL)
  3. extractionextracted with ethyl acetate (2×20 mL)
  4. washThe organic layer was washed with brine (10 mL)
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4d5ec9ec0fd54b558aa1535df9962e52
Source dataset
uspto-grants-2014_12
Patent number
US08906913B2

Reaction notes

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