Dichloromethane → methyl 1-(4-fluorophenyl)-1H-indazole-5-carboxylate

HRID 218173Notes

Reaction equation

HRID 218173 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([OH:19])=[O:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.Cl[CH2:21]Cl.C[Si](C=[N+]=[N-])(C)C>CO.C1COCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([O:19][CH3:21])=[O:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 167693TrimethylsilyldiazomethaneHCID 596259981-(4-fluorophenyl)-1H-indazole-5-carboxylic acid

Product 1

HCID 67006037methyl 1-(4-fluorophenyl)-1H-indazole-5-carboxylateYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of the 1-(4-fluorophenyl)-1H-indazole-5-carboxylic acid (0.22 g, 0.81 mmol) in methanol (5 mL), THF (5 mL), and dichloromethane (5 mL) was added (trimethylsilyl)diazomethane solution (2M in diethyl ether, 1 mL, 2 mmol) dropwise at rt. The reaction mixture was stirred at rt for 1 hr and carefully quenched by the slow addition of acetic acid. Concentration under reduced pressure and titration with methanol gave methyl 1-(4-fluorophenyl)-1H-indazole-5-carboxylate (0.16 g, 0.59 mmol, 73% yield) as a white solid.

Workup

  1. customcarefully quenched by the slow addition of acetic acid
  2. concentrationConcentration under reduced pressure and titration with methanol

Sources & evidence

ORD record
ord-b12ecaea493745ed9c3a366232dbaf61
Source dataset
uspto-grants-2012_06
Patent number
US08198311B2

Reaction notes

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