Iodoethane → HCID 178469302, compound

HRID 1880350Notes

Reaction equation

HRID 1880350 reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[C:6]([OH:16])[CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=2)[NH:4][N:3]=1.[H-].[Na+].I[CH2:20]C>CN(C=O)C.CCOC(C)=O>[CH3:20][O:16][C:6]1[CH:7]=[C:8]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:9]=[C:10]2[C:5]=1[NH:4][N:3]=[C:2]2[CH3:1]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178469296HCID 178469296, compound

Product 1

HCID 178469302HCID 178469302, compoundYield 58%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of ethyl 3-methyl-7-hydroxy-1H-indazole-5-carboxylate (0.84 g, 3.8 mmol) in DMF (25 mL) was added 60% oil dispersion of NaH (152 mg, 3.81 mmol). After stirring for 1 hour at 0° C., a solution of iodoethane (595 mg, 0.31 mL, 3.81 mmol) in DMF (3 mL) was added. The mixture was kept at 0° C. for several hours before allowing the mixture to warm to room temperature while stirring overnight. Dilute with EtOAc, wash with saturated aqueous NaHCO3, water, saturated aqueous NaCl and the organic extract was dried over Na2SO4, filtered and concentrated. The crude material was purified by CombiFlash (80 g column, 0-30% EtOAc/hexanes gradient) to provide ethyl 7-methoxy-3-methyl-1H-indazole-5-carboxylate (516 mg, 55%).

Workup

  1. waitThe mixture was kept at 0° C. for several hours
  2. temperatureto warm to room temperature
  3. stirringwhile stirring overnight
  4. washwash with saturated aqueous NaHCO3, water, saturated aqueous NaCl
  5. extractionthe organic extract
  6. dry with materialwas dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude material was purified by CombiFlash (80 g column, 0-30% EtOAc/hexanes gradient)

Sources & evidence

ORD record
ord-18af3e98d5f947ebb3e459515bd139fc
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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