Triethylamine → 2-(1-Azidoethyl)-5-fluoropyridine

HRID 1641396Notes

Reaction equation

HRID 1641396 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8](O)[CH3:9])=[N:6][CH:7]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:23]=[N+:24]=[N-:25].[Na+]>C(Cl)Cl.O>[N:23]([CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][N:6]=1)[CH3:9])=[N+:24]=[N-:25]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 591868831-(5-Fluoropyridin-2-yl)ethan-1-ol

Product 1

HCID 866248112-(1-Azidoethyl)-5-fluoropyridine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

1-(5-Fluoropyridin-2-yl)ethanol (Method 2; 7.5 g, 53.1 mmol) and triethyl amine (9.3 ml, 66.4 mmol) in anhydrous DCM (50 ml) was added methanesulfonyl chloride (4.5 ml, 58.5 mmol) at 0° C. After adding, the reaction was warmed to room temperature and stirred at room temperature for 2 hours. The solvent was removed. The residue was dissolved in anhydrous DMF (50 ml) and sodium azide (6.9 g, 106 mmol) was added. The reaction stirred at room temperature for 2 hours. Water (50 ml) was added and extracted with ether (2×75 ml).

Workup

  1. additionAfter adding
  2. customThe solvent was removed
  3. dissolutionThe residue was dissolved in anhydrous DMF (50 ml)
  4. stirringThe reaction stirred at room temperature for 2 hours
  5. extractionextracted with ether (2×75 ml)

Sources & evidence

ORD record
ord-aa604c257c0b4f24810e1e9f139e511e
Source dataset
uspto-grants-2012_02
Patent number
US08114989B2

Reaction notes

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