Sodium borohydride → (1-(3-methoxypropyl)-1H-indazol-6-yl)methanol

HRID 660366Notes

Reaction equation

HRID 660366 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([C:15](OC)=[O:16])[CH:13]=2)[CH:8]=[N:7]1.[BH4-].[Na+]>CO>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[C:12]([CH2:15][OH:16])[CH:13]=2)[CH:8]=[N:7]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68632252methyl 1-(3-methoxypropyl)-1H-indazol-6-carboxylate

Product 1

HCID 68502114(1-(3-methoxypropyl)-1H-indazol-6-yl)methanolYield 95.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 1-(3-methoxypropyl)-1H-indazole-6-carboxylate (1.26 g, 5 mmol) in MeOH (15 mL), NaBH4 (1.52 g, 40 mmol) was added in portions such that the temperature remained below 40° C. The mixture was stirred at rt for 12 h. TLC showed the starting material had been consumed. The solvent was removed in vacuo and the residue was partitioned between water and EtOAc. The organic layers were washed with H2O and brine, dried over Na2SO4, and evaporated to produce (1-(3-methoxypropyl)-1H-indazol-6-yl)methanol (1.05 g, 95%), which was used in the next step without purification.

Workup

  1. customremained below 40° C
  2. customhad been consumed
  3. customThe solvent was removed in vacuo
  4. customthe residue was partitioned between water and EtOAc
  5. washThe organic layers were washed with H2O and brine
  6. dry with materialdried over Na2SO4
  7. customevaporated

Sources & evidence

ORD record
ord-53b34fe4364d404696112fcb08559d04
Source dataset
uspto-grants-2011_12
Patent number
US08084485B2

Reaction notes

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