Iodoethane → HCID 178469308, compound

HRID 1880383Notes

Reaction equation

HRID 1880383 reaction equation
[CH2:1]([C:3]1[C:11]2[C:6](=[C:7]([OH:17])[CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=2)[NH:5][N:4]=1)[CH3:2].[H-].[Na+].I[CH2:21][CH3:22].[CH3:23][CH2:24]OC(C)=O>CN(C=O)C>[CH2:21]([O:17][C:7]1[CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=[C:11]2[C:6]=1[NH:5][N:4]=[C:3]2[CH2:1][CH3:2])[CH3:22].[CH2:23]([O:17][C:7]1[CH:8]=[C:9]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:10]=[C:11]2[C:6]=1[N:5]([CH2:21][CH3:22])[N:4]=[C:3]2[CH2:1][CH3:2])[CH3:24]

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 178469297HCID 178469297, compound

Product 2

HCID 66920474HCID 66920474, compoundHCID 178469308HCID 178469308, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a 0° C. solution of ethyl 3-ethyl-7-hydroxy-1H-indazole-5-carboxylate (prepared as described in Acid Preparation 2) (932 mg, 3.98 mmol) in DMF (28 mL) was added 60% NaH oil dispersion (159 mg, 3.98 mmol). This mixture was stirred at 0° C. for 1 hour before the dropwise addition of a solution of iodoethane (0.32 mL, 3.98 mmol) in DMF (3 mL). The mixture was kept at 0° C. for several hours before removal of the cooling bath and allowing the reaction to warm to room temperature while stirring overnight. The reaction was diluted with EtOAc, washed with saturated aqueous NaHCO3, saturated aqueous NaCl, the organic extract was then dried over Na2SO4, filtered and concentrated. Purify by CombiFlash (80 g column, 0-30% EtOAc/hexanes) to provide ethyl 7-ethoxy-3-ethyl-1H-indazole-5-carboxylate (389 mg, 37%) and ethyl 7-ethoxy-1,3-diethyl-1H-indazole-5-carboxylate (202 mg).

Workup

  1. customThe mixture was kept at 0° C. for several hours before removal of the cooling bath
  2. customthe reaction
  3. washwashed with saturated aqueous NaHCO3, saturated aqueous NaCl
  4. extractionthe organic extract
  5. dry with materialwas then dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurify by CombiFlash (80 g column, 0-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-fabca2f7ac1e4181bc17e8e42b8376df
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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