Sodium borohydride → HCID 178497394, compound

HRID 591686Notes

Reaction equation

HRID 591686 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[CH:14]=[O:15])=[O:4].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[NH:10][N:9]=[C:8]2[CH2:14][OH:15])=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178497393HCID 178497393, compound

Product 1

HCID 178497394HCID 178497394, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 3-formyl-1H-indazole-5-carboxylic acid methyl ester (0.37 g, 1.80 mmol) in anhydrous methanol (15 mL) was added sodium borohydride (68 mg, 1.80 mmol) in small portions at 0° C. After the addition, the reaction mixture was stirred at 0° C. for 30 minutes. Solvent was evaporated; water (100 mL) was added and the mixture was extracted with ethyl acetate (150 mL). The organic phase was washed with brine (100 mL) and dried over anhydrous Na2SO4. Solvent was evaporated to give 3-hydroxymethyl-1H-indazole-5-carboxylic acid methyl ester as a yellow solid. Yield: 0.32 g (87%).

Workup

  1. additionAfter the addition
  2. customSolvent was evaporated
  3. additionwater (100 mL) was added
  4. extractionthe mixture was extracted with ethyl acetate (150 mL)
  5. washThe organic phase was washed with brine (100 mL)
  6. dry with materialdried over anhydrous Na2SO4
  7. customSolvent was evaporated

Sources & evidence

ORD record
ord-6ba46c8591d347c3ac8b79ea76850625
Source dataset
uspto-grants-2016_01
Patent number
US09238640B2

Reaction notes

Loading…