Trimethylsilyldiazomethane → methyl 1H-indazole-4-carboxylate

HRID 2382930Notes

Reaction equation

HRID 2382930 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([C:10]([OH:12])=[O:11])[C:4]=2[CH:3]=[N:2]1.[CH3:13][Si](C=[N+]=[N-])(C)C>CO.C1(C)C=CC=CC=1>[CH3:13][O:11][C:10]([C:5]1[C:4]2[CH:3]=[N:2][NH:1][C:9]=2[CH:8]=[CH:7][CH:6]=1)=[O:12]

Participants

5

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 219823231H-indazole-4-carboxylic acid

Product 1

HCID 6623327methyl 1H-indazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent2×

Procedure

Indazole-4-carboxylic acid (2.00 g, 12.3 mmol) was suspended in methanol (20 mL) and toluene (30 mL) at room temperature. A solution of 2 M trimethylsilyl diazomethane (12 mL, 24 mmol) in toluene was added slowly and the mixture was stirred at room temperature until the solution turned yellow. The reaction was quenched with concentrated acetic acid (5 mL) and the solvent was removed in vacuo. The residue was purified by silica gel chromatography eluting with a gradient of 0-30% ethyl acetate in hexanes to afford 1H-indazole-4-carboxylic acid methyl ester.

Workup

  1. customat room temperature
  2. customThe reaction was quenched with concentrated acetic acid (5 mL)
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified by silica gel chromatography
  5. washeluting with a gradient of 0-30% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-990b81bdd88e42fdb3752cba5f103747
Source dataset
uspto-grants-2012_09
Patent number
US08263597B2

Reaction notes

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