Sodium borohydride → (1-Boc-6-fluoro-5-indazolyl)methanol

HRID 1914773Notes

Reaction equation

HRID 1914773 reaction equation
[F:1][C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[N:7][N:8]2[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[CH:4][C:3]=1[CH:18]=[O:19].[BH4-].[Na+]>CO.O.CCOC(C)=O>[OH:19][CH2:18][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][C:2]=1[F:1])[N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[N:7]=[CH:6]2

Participants

6

Reactant 2

HCID 4311764Sodium borohydrideHCID 59490926HCID 59490926, compound

Product 1

HCID 59490881(1-Boc-6-fluoro-5-indazolyl)methanolYield 84.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of tert-butyl 6-fluoro-5-formyl-1H-indazole-1-carboxylate (29E, 3.55 g, 13.4 mmol) in methanol (50.00 mL) was treated with NaBH4 (1.02 g, 26.9 mmol) at 0° C. and stirred for 1 h. The reaction mixture was diluted with water and EtOAc (500 mL). The organic layer was separated and washed with aq. HCl (1M, 200 mL), aq. NaOH (1M, 200 mL) brine (200 mL) dried (MgSO4), filtered, concentrated in vacuo and resulting residue was purified using chromatography (SiO2, EtOAc/hexanes) to yield tert-butyl 5-(hydroxymethyl)-6-fluoro-1H-indazole-1-carboxylate (29F, 3.00 g; Yield=83.9%) as a colorless solid.

Workup

  1. customThe organic layer was separated
  2. washwashed with aq. HCl (1M, 200 mL), aq. NaOH (1M, 200 mL) brine (200 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customresulting residue
  7. customwas purified

Sources & evidence

ORD record
ord-02e48e656a1f4188a2636d4363fd43a2
Source dataset
uspto-grants-2013_12
Patent number
US08614229B2

Reaction notes

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