Dimethylformamide → Methyl 3-iodo-1-methyl-1H-indazole-6-carboxylate

HRID 1096999Notes

Reaction equation

HRID 1096999 reaction equation
CI.C[N:4]([CH:6]=O)[CH3:5].[I:8][C:9]1[C:17]2C(=[CH:13][C:14]([C:18]([O:20][CH2:21]C)=[O:19])=[CH:15][CH:16]=2)N[N:10]=1.C([O-])([O-])=O.[K+].[K+]>CCCCCC.C(OCC)(=O)C.CO>[I:8][C:9]1[C:17]2[C:6](=[CH:13][C:14]([C:18]([O:20][CH3:21])=[O:19])=[CH:15][CH:16]=2)[N:4]([CH3:5])[N:10]=1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium Carbonate2×HCID 178468648HCID 178468648, compound

Product 1

HCID 57931017Methyl 3-iodo-1-methyl-1H-indazole-6-carboxylate

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

In a 100-mL egg plant-type flask, MeI (381 mL, 6 mmol) was added to a DMF solution (10 ml) of ethyl 3-iodo-1H-indazole-6-carboxylate (948 mg, 3 mmol) and K2CO3 (830 mg, 6 mmol), and stirred overnight at room temperature. Further, and K2CO3 (830 mg, 6 mmol) and methyl iodide (381 μL, 6 mmol) were added to it, and stirred at 50° C. for 1 hour. After the starting materials disappeared, methanol was added to the reaction solution and stirred at that temperature for 30 minutes. This was diluted with a mixed solvent of hexane and ethyl acetate, and washed with water and saturated saline water in that order, dried with sodium sulfate, filtered, concentrated and purified through silica gel column chromatography to obtain the title compound as a colorless solid.

Workup

  1. stirringstirred at 50° C. for 1 hour
  2. stirringstirred at that temperature for 30 minutes
  3. washwashed with water and saturated saline water in that order
  4. dry with materialdried with sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified through silica gel column chromatography

Sources & evidence

ORD record
ord-15d2bbd61de048bca287495f53ff91dd
Source dataset
uspto-grants-2012_03
Patent number
US08138197B2

Reaction notes

Loading…