Potassium Iodide → 6-amino-2-(4-methoxy-benzyl)-5-methyl-2H-indazole-7-carboxylic acid

HRID 1907145Notes

Reaction equation

HRID 1907145 reaction equation
[NH2:1][C:2]1[C:10]([C:11]([OH:13])=[O:12])=[C:9]2[C:5]([CH:6]=[N:7][NH:8]2)=[CH:4][C:3]=1[CH3:14].[Na].[CH3:16][O:17][C:18]1[CH:25]=[CH:24][C:21]([CH2:22]Cl)=[CH:20][CH:19]=1.[I-].[K+]>CN(C)C=O>[NH2:1][C:2]1[C:3]([CH3:14])=[CH:4][C:5]2[C:9]([C:10]=1[C:11]([OH:13])=[O:12])=[N:8][N:7]([CH2:22][C:21]1[CH:24]=[CH:25][C:18]([O:17][CH3:16])=[CH:19][CH:20]=1)[CH:6]=2

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 699934-Methyloxybenzyl chlorideHCID 5360545SodiumHCID 468557186-amino-5-methyl-2H-indazole-7-carboxylic acid

Product 1

HCID 585004296-amino-2-(4-methoxy-benzyl)-5-methyl-2H-indazole-7-carboxylic acid

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 6-amino-5-methyl-1H-indazole-7-carboxylic acid (0.956 g, 5 mmol) in dimethylformamide (4 ml) was added sodium hydrogenocarbonate (0.462 g, 5.5 mmol) and the resulting mixture was stirred at 40° C. for 15 minutes before 4-methoxybenzyl chloride (0.861 g, 5.5 mmol) was introduced. A catalytic amount of potassium iodide was added and the mixture was stirred for 18 hours at that temperature. After cooling down, the crude mixture was placed on top of a silica gel column and the product was purified by flash chromatography using a gradient starting from 50% ethyl acetate-50% cyclohexane to 100% ethyl acetate, then 1% acetic acid in ethyl acetate. The fractions containing the desired compound were evaporated and the residue was triturated with diethyl ether and filtered to yield light orange crystals.

Workup

  1. additionwas introduced
  2. temperatureAfter cooling down
  3. customthe product was purified by flash chromatography
  4. additionThe fractions containing the desired compound
  5. customwere evaporated
  6. customthe residue was triturated with diethyl ether
  7. filtrationfiltered
  8. customto yield light orange crystals

Sources & evidence

ORD record
ord-9d1fc43bf4a54b69a3823e96147949bf
Source dataset
uspto-grants-2013_12
Patent number
US08598078B2

Reaction notes

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