Sodium hydride → (R)-1-methyl-3-(3-oxiranylmethoxy-phenyl)-1H-thieno[3,2-c]pyrazole

HRID 1246559Notes

Reaction equation

HRID 1246559 reaction equation
[H-].[Na+].[CH3:3][N:4]1[C:8]2[CH:9]=[CH:10][S:11][C:7]=2[C:6]([C:12]2[CH:13]=[C:14]([OH:18])[CH:15]=[CH:16][CH:17]=2)=[N:5]1.S(C1C=CC(C)=CC=1)(O[CH2:23][C@@H:24]1[O:26][CH2:25]1)(=O)=O.[Cl-].[NH4+]>O.CN(C)C=O>[CH3:3][N:4]1[C:8]2[CH:9]=[CH:10][S:11][C:7]=2[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH2:23][C@H:24]3[CH2:25][O:26]3)[CH:13]=2)=[N:5]1

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 154187Glycidyl tosylate, (R)-HCID 21915373HCID 21915373, compound

Product 1

HCID 58720310(R)-1-methyl-3-(3-oxiranylmethoxy-phenyl)-1H-thieno[3,2-c]pyrazoleYield 60.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (0.14 g, 0.0059 mol) at 0° C. under nitrogen to a stirred solution of 3-(1-methyl-1H-thieno[3,2-c]pyrazol-3-yl)phenol (example 3) (1.13 g, 0.0049 mol) and dimethylformamide (50 mL). Stir 15 min. and add (R)-(−)-glycidyl tosylate (1.12 g, 0.0049 mol, Aldrich Chemical Company), and then stir overnight at room temperature. Pour into water (400 mL), add a little ammonium chloride and extract with ethyl acetate. Dry (Na2SO4), filter and evaporate the extract, and purify the residue by flash chromatography (silica gel, elute with dichloromethane and then with 2% methanol in dichloromethane). Concentrate the desired fractions to afford the title compound as a white solid (0.85 g, 60% yield).

Workup

  1. stirringstir overnight at room temperature
  2. extractionextract with ethyl acetate
  3. dry with materialDry (Na2SO4)
  4. filtrationfilter
  5. customevaporate the extract
  6. custompurify the residue by flash chromatography (silica gel
  7. washelute with dichloromethane
  8. concentrationConcentrate the desired fractions

Sources & evidence

ORD record
ord-1d0af1f6d6ed4c14a6d20e69b6d2ac0c
Source dataset
uspto-grants-2006_10
Patent number
US07125903B1

Reaction notes

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