Dimethylformamide → HCID 66920473, compound

HRID 1880387Notes

Reaction equation

HRID 1880387 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11]([OH:13])=[O:12])[CH:5]=[C:6]2[C:10]=1[NH:9][N:8]=[CH:7]2.[C:14]([O-])([O-])=O.[K+].[K+].IC.C[N:23]([CH:25]=O)[CH3:24]>CCOC(C)=O>[CH3:24][N:23]1[C:25]2[C:6](=[CH:5][C:4]([C:11]([O:13][CH3:14])=[O:12])=[CH:3][C:2]=2[CH3:1])[CH:7]=[N:8]1.[CH3:24][N:23]1[CH:25]=[C:6]2[C:10]([C:2]([CH3:1])=[CH:3][C:4]([C:11]([O:13][CH3:14])=[O:12])=[CH:5]2)=[N:9]1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 534085037-Methyl-1H-indazole-5-carboxylic acid

Product 2

HCID 66920473HCID 66920473, compoundYield 35%HCID 66920600HCID 66920600, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 7-methyl-1H-indazole-5-carboxylic acid (356 mg, 2.0 mmol) in DMF (6 mL) was added K2CO3 (0.85 g, 6.2 mmol) and iodomethane (0.45 mL, 7.2 mmol). The mixture was stirred at room temperature for 4 hours and then heated at 50° C. overnight. The reaction was cooled to room temperature, diluted with EtOAc and washed with saturated aqueous NaCl. The organic extract was concentrated and purified by Biotage chromatography (40 S column, 25-50% EtOAc/heptane) to afford methyl 1,7-dimethyl-1H-indazole-5-carboxylate (91 mg, 22%) and methyl 2,7-dimethyl-2H-indazole-5-carboxylate (141 mg, 35%).

Workup

  1. temperatureheated at 50° C. overnight
  2. temperatureThe reaction was cooled to room temperature
  3. washwashed with saturated aqueous NaCl
  4. extractionThe organic extract
  5. concentrationwas concentrated
  6. custompurified by Biotage chromatography (40 S column, 25-50% EtOAc/heptane)

Sources & evidence

ORD record
ord-dc0f930a293a4585be0f2f023126cca8
Source dataset
uspto-grants-2012_11
Patent number
US08318762B2

Reaction notes

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