Ammonium Chloride → 1-Azido-2-(2-bromo-5-fluoro-pyridin-4-yl)-propan-2-ol

HRID 474081Notes

Reaction equation

HRID 474081 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]([OH:16])([CH3:15])[CH2:9]OS(C)(=O)=O)[C:5]([F:17])=[CH:4][N:3]=1.[N-:18]=[N+:19]=[N-:20].[Na+].[NH4+].[Cl-]>C(O)C.O.CC(OC)(C)C>[N:18]([CH2:9][C:8]([C:6]1[C:5]([F:17])=[CH:4][N:3]=[C:2]([Br:1])[CH:7]=1)([OH:16])[CH3:15])=[N+:19]=[N-:20]

Participants

7

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 86668051Methanesulfonic acid 2-(2-bromo-5-fluoro-pyridin-4-yl)-2-hydroxy-propyl ester

Product 1

HCID 866680521-Azido-2-(2-bromo-5-fluoro-pyridin-4-yl)-propan-2-ol

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of methanesulfonic acid 2-(2-bromo-5-fluoro-pyridin-4-yl)-2-hydroxy-propyl ester (10.36 g, 31.6 mmol) in ethanol (160 ml) was added NaN3 (5.13 g, 79.0 mmol) and NH4Cl (8.44 g, 158.0 mmol). The reaction mixture was stirred at 80° C. for 20 h. The reaction mixture was diluted with H2O and TBME and the phases were separated. The aq. phase was twice reextracted with TBME, the combined org. phases were washed with brine, dried over Na2SO4, filtered and concentrated. HPLC RtH4=0.89 min; ESIMS: 275, 277 [(M+H)+]; 1H NMR (400 MHz, CDCl3): δ 8.20 (d, 1H), 7.80 (d, 1H), 3.81 (d, 1H), 3.65 (d, 1H), 1.61 (s, 3H).

Workup

  1. customthe phases were separated
  2. washphases were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customHPLC RtH4=0.89 min

Sources & evidence

ORD record
ord-7e4a85788f3f4f4694d1651d59b1eb78
Source dataset
uspto-grants-2014_01
Patent number
US08637508B2

Reaction notes

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