Methyl iodide → Methyl 1-methyl-1H-indazole-5-carboxylate

HRID 1880385Notes

Reaction equation

HRID 1880385 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[N:4]1.I[CH3:17]>CN(C=O)C>[CH3:17][N:3]1[C:11]2[C:6](=[CH:7][C:8]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:10]=2)[CH:5]=[N:4]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22260640Methyl 1H-indazole-5-carboxylate

Product 1

HCID 37818676Methyl 1-methyl-1H-indazole-5-carboxylateYield 38%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 60% NaH oil dispersion (87 mg, 2.2 mmol) in DMF (4 mL) was added methyl 1H-indazole-5-carboxylate (264 mg, 1.50 mmol). The mixture was stirred at room temperature for 1 hour before the dropwise addition of iodomethane (0.11 mL, 1.8 mmol). The mixture was stirred at room temperature for 2 hours, concentrated and the residue was purified by Biotage chromatography (40S column, 15% acetone/heptane) to afford methyl 1-methyl-1H-indazole-5-carboxylate (107 mg, 38%).

Workup

  1. concentrationconcentrated
  2. customthe residue was purified by Biotage chromatography (40S column, 15% acetone/heptane)

Sources & evidence

ORD record
ord-5d58199b1e18474facd69ca6b3e136c3
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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