Methyl iodide → Methyl 4-[3-methoxy6-nitroindazol-1-ylmethyl]-3-methoxybenzoate

HRID 1080788Notes

Reaction equation

HRID 1080788 reaction equation
[OH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=2[O:25][CH3:26])[N:3]=1.[Na].I[CH3:29]>CO.C(OCC)(=O)C>[CH3:29][O:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[CH:8][CH:9]=2)[N:4]([CH2:14][C:15]2[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=2[O:25][CH3:26])[N:3]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 178497911HCID 178497911, compound

Product 1

HCID 23365859Methyl 4-[3-methoxy6-nitroindazol-1-ylmethyl]-3-methoxybenzoateYield 28%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Indazole (T) (1.68 g.) was added to a solution of sodium (0.108 g.) in methanol (1.0 ml.). After stirring for 5 minutes, iodomethane (0.32 ml.) was added and stirring continued for 18 hours. The mixture was diluted with ethyl acetate, washed with water and brine, then dried (MgSO4) and evaporated. The residue was purified by flash chromatography on silica gel (130 g.), eluting with 2:98 v/v ethyl acetate:dichloromethane to give methyl 4-[3-methoxy6-nitroindazol-1-ylmethyl]-3-methoxybenzoate (U) (0.481 g., 28%) as a yellow solid, with satisfactory NMR spectral data.

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe residue was purified by flash chromatography on silica gel (130 g.)
  7. washeluting with 2:98 v/v ethyl acetate

Sources & evidence

ORD record
ord-0757266c581043af95a5c5a107984c28
Source dataset
uspto-grants-1996_12
Patent number
US05583152

Reaction notes

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