Ammonium Chloride → HCID 86668033, compound

HRID 538323Notes

Reaction equation

HRID 538323 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([OH:16])([CH3:15])[CH2:9]OS(C)(=O)=O)[C:5]([F:17])=[CH:4][CH:3]=1.[Cl-].[NH4+].[N-:20]=[N+:21]=[N-:22].[Na+]>C(O)C.C(OCC)(=O)C>[N:20]([CH2:9][C:8]([C:6]1[C:5]([F:17])=[CH:4][CH:3]=[C:2]([Br:1])[N:7]=1)([OH:16])[CH3:15])=[N+:21]=[N-:22]

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86668032HCID 86668032, compound

Product 1

HCID 86668033HCID 86668033, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of methanesulfonic acid 2-(6-bromo-3-fluoro-pyridin-2-yl)-2-hydroxy-propyl ester (5 g, 15.24 mmol), ammonium chloride (4.08 g, 76 mmol) and sodium azide (2.476 g, 38.1 mmol) in ethanol (100 ml) was stirred at 80° C. for 20 hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over sodium sulfate, filtered and evaporated. 3.1 g (74% yield). TLC (cyclohexane/ethyl acetate 9:1) Rf=0.35; LCMS RtH5=0.97 min. (ES+ 275, 277); 1H-NMR (360 MHz, CDCl3): 7.51 (dd, 1H), 7.36 (dd, 1H), 5.18 (s broad, 1H, OH), 3.68-3.60 (AB system, 2H), 1.59 (s, 3H, CH3).

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. customevaporated
  5. customLCMS RtH5=0.97 min. (ES+ 275, 277)

Sources & evidence

ORD record
ord-e49ac9a3ba7c47b4b574890b039378cb
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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