Iodoethane → 1,3-diethyl-1H-indazole-6-carboxylic acid methoxy-methyl-amide

HRID 2240179Notes

Reaction equation

HRID 2240179 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].ICC.[CH3:10][O:11][N:12]([CH3:26])[C:13]([C:15]1[CH:23]=[C:22]2[C:18]([C:19]([CH2:24][CH3:25])=[N:20][NH:21]2)=[CH:17][CH:16]=1)=[O:14].C(OCC)(=O)C>C1COCC1>[CH3:10][O:11][N:12]([CH3:26])[C:13]([C:15]1[CH:23]=[C:22]2[C:18]([C:19]([CH2:24][CH3:25])=[N:20][N:21]2[CH2:1][CH3:2])=[CH:17][CH:16]=1)=[O:14]

Participants

6

Reactant 4

HCID 6340IodoethaneHCID 8857Ethyl AcetateHCID 23665647Potassium tert-butoxideHCID 178438012HCID 178438012, compound

Product 1

HCID 598108331,3-diethyl-1H-indazole-6-carboxylic acid methoxy-methyl-amideYield 111.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of potassium tert-butoxide (0.144 g, 1.28 mmol) and iodoethane (0.20 g, 1.28 mmol) in THF (1 mL) was added to a solution of 3-ethyl-1H-indazole-6-carboxylic acid methoxy-methyl-amide (0.20 g, 0.86 mmol) in THF (3 mL) and the resulting mixture stirred at room temperature for 16 hours. Ethyl acetate (30 mL) was then added and the product was extracted with 0.5 N HCl (10 mL). The aqueous layer was then re-extracted with ethyl acetate (30 mL). The organics were combined, dried, filtered and concentrated to afford 250 mg of 1,3-diethyl-1H-indazole-6-carboxylic acid methoxy-methyl-amide that was used without further purification.

Workup

  1. extractionthe product was extracted with 0.5 N HCl (10 mL)
  2. extractionThe aqueous layer was then re-extracted with ethyl acetate (30 mL)
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-8cf9140a54db435b80cce6c0da88dc9f
Source dataset
uspto-grants-2010_05
Patent number
US07723348B2

Reaction notes

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