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

HRID 386063

Reaction equation

HRID 386063 reaction equation
[BH4-].[Na+].C([O:5][C:6](=O)[CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Br:19])[N:14]=2)[N:10]=[N:9]1)C>CO.O>[Br:19][C:15]1[N:14]=[C:13]([C:11]2[N:10]=[N:9][N:8]([CH2:7][CH2:6][OH:5])[CH:12]=2)[CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59525977ethyl[4-(6-bromopyridin-2-yl)-1H-1,2,3-triazol-1-yl]acetate

Product 1

HCID 595263122-[4-(6-Bromopyridin-2-yl)-1H-1,2,3-triazol-1-yl]ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Procedure

To a solution of NaBH4 (60 mg, 1.58 mmol) in MeOH (3.0 mL) at room temperature was added ethyl[4-(6-bromopyridin-2-yl)-1H-1,2,3-triazol-1-yl]acetate (245 mg, 0.79 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×). The combined organic layers were washed with brine, dried (MgSO4), filtered, and evaporated. Flash chromatography (20-100% EtOAc/hexanes) afforded the title compound as a colorless gum.

Workup

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

Sources & evidence

ORD record
ord-37c3845d1eeb4d459582c137cdd8120d
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Linked notes

Loading…