Sodium Azide → 5-(1-Azido-ethyl)-2-fluoro-4-iodo-pyridine

HRID 1640882Notes

Reaction equation

HRID 1640882 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[F:5][C:6]1[N:11]=[CH:10][C:9]([CH:12](OS(C)(=O)=O)[CH3:13])=[C:8]([I:19])[CH:7]=1>CCCC[N+](CCCC)(CCCC)CCCC.[Br-].CN(C=O)C.C(Cl)(Cl)Cl>[N:1]([CH:12]([C:9]1[C:8]([I:19])=[CH:7][C:6]([F:5])=[N:11][CH:10]=1)[CH3:13])=[N+:2]=[N-:3]

Participants

6

Reactant 2

HCID 33557Sodium AzideHCID 86641872Methanesulfonic acid 1-(6-fluoro-4-iodo-pyridin-3-yl)-ethyl ester

Product 1

HCID 866418735-(1-Azido-ethyl)-2-fluoro-4-iodo-pyridineYield 76%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Add sodium azide (0.45 g, 7 mmol) and tetra-N-butylammonium bromide (0.12 g, 0.4 mmol) to a solution of methanesulfonic acid 1-(6-fluoro-4-iodo-pyridin-3-yl)-ethyl ester (1.2 g, 3.5 mmol) in DMF (20 mL) at 0° C. Stir the mixture at RT for 42 h. Dilute the reaction mixture with chloroform. Wash the organic phase with water and saturated aqueous sodium chloride. Dry the organic phase over sodium sulfate. Concentrate the solution in vacuo. Purify by column chromatography (20% ethyl acetate in hexane) to afford the title compound as a white solid (0.77 g, 76%). 1H NMR (400 MHz-CDCl3) δ 1.56 (d, J=6.8 Hz, 1H), 4.90 (m, 1H), 7.45 (d, J=3.2 Hz, 1H), 8.17 (s, 3H).

Workup

  1. washWash the organic phase with water and saturated aqueous sodium chloride
  2. dry with materialDry the organic phase over sodium sulfate
  3. concentrationConcentrate the solution in vacuo
  4. customPurify by column chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-f5442cef09a44699ab71b3ee77bceaf3
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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