Sodium borohydride → (+/-)-1-(6-Bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethanol

HRID 2099763Notes

Reaction equation

HRID 2099763 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8](=[O:28])[CH2:9][C:10]2[CH:18]=[C:17]([CH3:19])[C:16]3[C:12](=[CH:13][N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:27])([CH3:26])[CH3:25])[N:15]=3)[CH:11]=2)[CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO>[Br:1][C:2]1[N:7]=[C:6]([CH:8]([OH:28])[CH2:9][C:10]2[CH:18]=[C:17]([CH3:19])[C:16]3[C:12](=[CH:13][N:14]([CH2:20][O:21][CH2:22][CH2:23][Si:24]([CH3:25])([CH3:27])[CH3:26])[N:15]=3)[CH:11]=2)[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 577945841-(6-Bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethanone

Product 1

HCID 57794705(+/-)-1-(6-Bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethanolYield 102%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (±)-1-(6-bromopyridin-2-yl)-2-(7-methyl-2-((2-(trimethylsilyl)ethoxy)methyl)-2H-indazol-5-yl)ethanone (977 mg, 2.12 mmol) in methanol (10 mL) at room temperature under nitrogen was added sodium borohydride (97 mg, 2.55 mmol, 1.2 equiv) in one portion. The solution was stirred at room temperature for 1 h. Methanol was then removed under vacuum and the residue was partitioned between water and ethyl acetate. The organic layer was separated, washed with brine, dried and concentrated to give a light yellow oil (1 g, 100%). MS (ESI) [M+H]+=463. HPLC tR=1.93 min.

Workup

  1. customMethanol was then removed under vacuum
  2. customthe residue was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b7e1836c92d64234bcb3cea2660a8056
Source dataset
uspto-grants-2009_08
Patent number
US07569578B2

Reaction notes

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