Boron trifluoride → HCID 86661597, compound

HRID 1848353Notes

Reaction equation

HRID 1848353 reaction equation
[CH:1]1([O:6][C:7](=[O:24])[NH:8][CH2:9][C:10]2([C:13]3[N:23]=[C:16]4[C:17]([O:21][CH3:22])=[CH:18][CH:19]=[CH:20][N:15]4[N:14]=3)[CH2:12][CH2:11]2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[I:25]N1C(=O)CCC1=O.B(F)(F)F.[O-]S([O-])(=S)=O.[Na+].[Na+]>C([O-])(O)=O.[Na+]>[CH:1]1([O:6][C:7](=[O:24])[NH:8][CH2:9][C:10]2([C:13]3[N:23]=[C:16]4[C:17]([O:21][CH3:22])=[CH:18][CH:19]=[C:20]([I:25])[N:15]4[N:14]=3)[CH2:11][CH2:12]2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 4

HCID 6356Boron trifluorideHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 66707411HCID 66707411, compound

Product 1

HCID 86661597HCID 86661597, compound

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)-cyclopropylmethyl]-carbamic acid cyclopentyl ester was mixed with N-iodosuccinimide. BF3*2H2O was added at 0° C. The dark suspension was stirred at rt for 3 h after which it was poured onto a 1:1 solution of saturated Na2S2O3 and saturated NaHCO3 (20 mL). The aqueous phase was extracted with DCM (×2) 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 to afford [1-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-carbamic acid cyclopentyl ester.

Workup

  1. additionwas added at 0° C
  2. extractionThe aqueous phase was extracted with DCM (×2)
  3. washthe combined organic phases were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude product was purified by flash chromatography on silica

Sources & evidence

ORD record
ord-07b10d6ae6754d6e981c79cfeaab64b9
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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