Water → HCID 86614013, compound

HRID 253106Notes

Reaction equation

HRID 253106 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[Br:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1/[CH:17]=[CH:18]/[C:19]([N:21]([O:23][CH3:24])[CH3:22])=[O:20].O>CS(C)=O>[Br:9][C:10]1[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=1[CH:17]1[CH2:4][CH:18]1[C:19]([N:21]([O:23][CH3:24])[CH3:22])=[O:20]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 86614012HCID 86614012, compound

Product 1

HCID 86614013HCID 86614013, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent2×

Conditions

Temperature
25 °C

Procedure

Sodium hydride (60%, 122 mg, 3.05 mmol, Aldrich) was added to a suspension of trimethylsulfoxonium iodide (671 mg, 3.05 mmol, Aldrich) in DMSO (6 mL). The mixture was stirred at 25° C. for 30 min, and (E)-3-(2-bromo-5-fluorophenyl)-N-methoxy-N-methylacrylamide was added as a solution in DMSO (3 mL). The mixture was stirred at 25° C. for 12 h, then transferred to a separatory funnel with H2O (40 mL), and the title compound was extracted using 75% ether/hexane (3×40 mL). The organic layer was dried over sodium sulfate and concentrated. Purification by flash column chromatography (33% EtOAc/hexane) afforded the title compound as a colorless oil. MS m/z: 302 and 304 (M+1).

Workup

  1. stirringThe mixture was stirred at 25° C. for 12 h
  2. extractionthe title compound was extracted
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated
  5. customPurification by flash column chromatography (33% EtOAc/hexane)

Sources & evidence

ORD record
ord-79be1a644bc14331b5458a1d532200af
Source dataset
uspto-grants-2011_01
Patent number
US07872009B2

Reaction notes

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