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

HRID 2207554Notes

Reaction equation

HRID 2207554 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-4eaeba2a21994c7fa09142d05a398ae3
Source dataset
uspto-grants-2016_06
Patent number
US09376443B2

Reaction notes

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