Boron trifluoride → 1-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester

HRID 1848337Notes

Reaction equation

HRID 1848337 reaction equation
[CH2:1]([O:3][C:4]([C:6]1([C:9]2[N:19]=[C:12]3[C:13]([O:17][CH3:18])=[CH:14][CH:15]=[CH:16][N:11]3[N:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].[I:20]N1C(=O)CCC1=O.B(F)(F)F.[O-]S([O-])(=S)=O.[Na+].[Na+]>C([O-])(O)=O.[Na+]>[CH2:1]([O:3][C:4]([C:6]1([C:9]2[N:19]=[C:12]3[C:13]([O:17][CH3:18])=[CH:14][CH:15]=[C:16]([I:20])[N:11]3[N:10]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

6

Reactant 4

HCID 6356Boron trifluoride3×HCID 24477Sodium ThiosulfateHCID 120273N-Iodosuccinimide3×HCID 580746401-(8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester

Product 1

HCID 580746021-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Under an argon atmosphere 1-(8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropanecarboxylic acid ethyl ester (4.1 g, 13.7 mmol) was mixed with N-iodosuccinimide (4.9 g, 21.9 mmol). BF3*2H2O (7.0 mL, 110 mmol) was added at 20° C. The dark suspension was stirred at rt for 24 h. NIS (2.5 g) and BF3*2H2O (2.0 mL) were added and the suspension was stirred for 24H. NIS (2.5 g) and BF3*2H2O (2.0 mL) were added and the suspension was stirred for another 24 h after which it was poured onto a 1:1 solution of saturated Na2S2O3 and saturated NaHCO3 (300 mL). The aqueous phase was extracted with DCM and the combined organic phases were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica using DCM-EtOAc as eluent. The title compound was obtained as a colourless solid (4.1 g).

Workup

  1. stirringthe suspension was stirred for 24H
  2. stirringthe suspension was stirred for another 24 h after which it
  3. extractionThe aqueous phase was extracted with DCM
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-d570fb9b60fb41ddaa6759b32e360909
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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