Iodoethane → HCID 66920431, compound

HRID 1880414Notes

Reaction equation

HRID 1880414 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[H-].[Na+].I[CH2:19][CH3:20]>CN(C=O)C>[CH2:19]([O:1][C:2]1[CH:3]=[C:4]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2)[CH3:20]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 66523890HCID 66523890, compound

Product 1

HCID 66920431HCID 66920431, compoundYield 38.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of ethyl 7-hydroxy-1H-indazole-5-carboxylate (918 mg, 4.45 mmol) in DMF (35 mL) at 0° C. was added 60% oil dispersion of NaH (178 mg, 4.45 mmol). The mixture was aged for 1 hour at 0° C. before dropwise addition of a solution of iodoethane (694 mg, 0.36 mL, 4.45 mmol) in DMF (15 mL). The mixture was aged at 0° C. for several hours before removal of the ice bath. The reaction was allowed to warm to room temperature and aged overnight. The mixture was diluted with EtOAc, washed with water, saturated aqueous NaCl, dried over Na2SO4, filtered concentrated. Purify by silica gel chromatography (40 g column) eluting with 0-30% EtOAc/hexanes gradient to afford ethyl 7-ethoxy-1H-indazole-5-carboxylate (400 mg, 38%).

Workup

  1. customThe mixture was aged at 0° C. for several hours before removal of the ice bath
  2. additionThe mixture was diluted with EtOAc
  3. washwashed with water, saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurify by silica gel chromatography (40 g column)
  8. washeluting with 0-30% EtOAc/hexanes gradient

Sources & evidence

ORD record
ord-03915995f33d4131b99ba5f887efcdb0
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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