Dimethylformamide → HCID 58706535, compound

HRID 1716513Notes

Reaction equation

HRID 1716513 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C@@H:13]3[CH2:17][O:16][C:15](=[O:18])[NH:14]3)=[N:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:21]N(C)C=O.CI>O1CCCC1>[Br:1][C:2]1[N:7]=[C:6]([C:8]2[S:12][C:11]([C@@H:13]3[CH2:17][O:16][C:15](=[O:18])[N:14]3[CH3:21])=[N:10][CH:9]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 58706654HCID 58706654, compound

Product 1

HCID 58706535HCID 58706535, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(S)-4-[5-(6-bromopyridin-2-yl)thiazol-2-yl]oxazolidin-2-one (488 mg, 1.50 mmol) obtained in Step 4 and sodium hydride (60% oily, 72 mg, 1.80 mmol) were suspended in tetrahydrofuran (5 ml) and dimethylformamide (5 ml) in an Ar stream and methyl iodide (0.1 ml, 1.65 mmol) was added while ice-cooled and stirred at room temperature for 12 hours. After the reaction solution was concentrated, water was added and it was extracted with ethyl acetate. After the organic layer was washed with a saturated brine and dried over magnesium sulfate, it was concentrated and the residue was purified by flash chromatography on silica gel (chloroform:methanol=20:1) and the title compound (205 mg, 40%) was obtained.

Workup

  1. temperaturecooled
  2. concentrationAfter the reaction solution was concentrated
  3. additionwater was added
  4. extractionit was extracted with ethyl acetate
  5. washAfter the organic layer was washed with a saturated brine
  6. dry with materialdried over magnesium sulfate, it
  7. concentrationwas concentrated
  8. customthe residue was purified by flash chromatography on silica gel (chloroform:methanol=20:1)

Sources & evidence

ORD record
ord-07efe9c3676b4421807bbbdc43a8ec38
Source dataset
uspto-grants-2010_09
Patent number
US07803801B2

Reaction notes

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