Sodium Azide → 2-[6-(Azidomethyl)-2-pyridyl]propan-2-ol

HRID 876974Notes

Reaction equation

HRID 876974 reaction equation
Br[CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:12])([CH3:11])[CH3:10])[N:4]=1.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C)C=O>[N:13]([CH2:2][C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]([OH:12])([CH3:11])[CH3:10])[N:4]=1)=[N+:14]=[N-:15]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 667183882-(6-(Bromomethyl)pyridin-2-yl)propan-2-ol

Product 1

HCID 866553202-[6-(Azidomethyl)-2-pyridyl]propan-2-ol

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-Bromomethyl-6-(1-hydroxy-1-methylethyl)pyridine (7.61 g, 33 mmol) was dissolved in dimethylformamide (100 mL) and sodium azide (2.6 g, 39.7 mmol) added. After stirring the resultant mixture overnight at ambient temperature, the reaction was poured into dicholoromethane and washed well with water. The organic layer was dried (magnesium sulphate), filtered and concentrated to dryness. The resulting yellow oil (5.88 g, 93%) was used without further purification; NMR δH (400 MHz, CDCl3) 7.70 (1H, t, J 7.8 Hz), 7.30 (1H, d, J 8.0 Hz), 7.19 (1H, d, J 7.8 Hz), 4.82 (1H, br s), 4.42 (2H, s), 1.51 (6H, s); LC-MS Retention time 2.06 min, (M+H)+ 193.

Workup

  1. additionthe reaction was poured into dicholoromethane
  2. washwashed well with water
  3. dry with materialThe organic layer was dried (magnesium sulphate)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe resulting yellow oil (5.88 g, 93%) was used without further purification

Sources & evidence

ORD record
ord-7e0bc23bf1b8471c89e67d9826b2b1d9
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

Loading…