Sodium borohydride → 1-(6-Bromopyridin-2-yl)-1-[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]ethanol

HRID 386073Notes

Reaction equation

HRID 386073 reaction equation
[BH4-].[Na+].C([O:5][C:6](=O)[CH2:7][N:8]1[CH:12]=[C:11]([C:13]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([Br:22])[N:17]=2)([OH:15])[CH3:14])[N:10]=[N:9]1)C>CO.O>[Br:22][C:18]1[N:17]=[C:16]([C:13]([C:11]2[N:10]=[N:9][N:8]([CH2:7][CH2:6][OH:5])[CH:12]=2)([OH:15])[CH3:14])[CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59526331ethyl{4-[1-(6-bromopyridin-2-yl)-1-hydroxyethyl]-1H-1,2,3-triazol-1-yl}acetate

Product 1

HCID 595261461-(6-Bromopyridin-2-yl)-1-[1-(2-hydroxyethyl)-1H-1,2,3-triazol-4-yl]ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of NaBH4 (92 mg, 2.42 mmol) in MeOH (3.0 mL) at room temperature was added ethyl{4-[1-(6-bromopyridin-2-yl)-1-hydroxyethyl]-1H-1,2,3-triazol-1-yl}acetate (430 mg, 1.21 mmol) in MeOH (7.0 mL). The reaction was stirred at room temperature for 2 h. It was then diluted with water and extracted with EtOAc (2×) and 5:1 CH2Cl2:MeOH (5×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (0-5% MeOH/EtOAc) afforded the title compound as a colorless solid.

Workup

  1. extractionextracted with EtOAc (2×) and 5:1 CH2Cl2
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-874c620368584f1b852c08a811b26dee
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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