Sodium Azide → 2-(1-Azidoethyl)-4-bromopyridine

HRID 879581Notes

Reaction equation

HRID 879581 reaction equation
CS(O[CH:6]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][N:9]=1)[CH3:7])(=O)=O.[N-:15]=[N+:16]=[N-:17].[Na+]>CN(C=O)C.O>[N:15]([CH:6]([C:8]1[CH:13]=[C:12]([Br:14])[CH:11]=[CH:10][N:9]=1)[CH3:7])=[N+:16]=[N-:17]

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 86700398HCID 86700398, compound

Product 1

HCID 867003992-(1-Azidoethyl)-4-bromopyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirring solution of 1-(4-bromopyridin-2-yl)ethyl methanesulfonate (4.68 g, 16.71 mmol) in anhydrous DMF (45 mL) DMF was added sodium azide (2.17 g, 33.41 mmol) and stirred at room temperature for 2 hours. The reaction was then diluted with 80 mL of water, then extracted with EtOAc (2×75 mL). The organic extracts were combined, washed with water (50 mL) and brine (50 mL), dried over Na2SO4, and concentrated to give the crude product which was used directly without further purification. 1H NMR (400 MHz, CDCl3) δ 8.40 (d, J=5.2 Hz, 1H), 7.55 (s, 1H), 7.41 (d, J=5.2 Hz, 1H), 4.65 (q, J=6.8 Hz, 1H), 1.60 (dd, J=6.8, 0.8 Hz, 3H).

Workup

  1. extractionextracted with EtOAc (2×75 mL)
  2. washwashed with water (50 mL) and brine (50 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0bd85c82bc224668ab5789b12db8042f
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

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