Boron trifluoride → HCID 86661596, compound

HRID 1848351Notes

Reaction equation

HRID 1848351 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:9]=[C:10]([C:12]3([CH2:15][NH:16][C:17](=[O:21])[CH:18]([CH3:20])[CH3:19])[CH2:14][CH2:13]3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1.[I:22]N1C(=O)CCC1=O.B(F)(F)F.[O-]S([O-])(=S)=O.[Na+].[Na+]>C([O-])(O)=O.[Na+]>[I:22][C:6]1[N:5]2[N:9]=[C:10]([C:12]3([CH2:15][NH:16][C:17](=[O:21])[CH:18]([CH3:19])[CH3:20])[CH2:13][CH2:14]3)[N:11]=[C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6356Boron trifluorideHCID 24477Sodium ThiosulfateHCID 120273N-IodosuccinimideHCID 66707604HCID 66707604, compound

Product 1

HCID 86661596HCID 86661596, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Under an argon atmosphere N-[1-(8-Methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-isobutyramide (0.063 g, 0.22 mmol) was mixed with N-iodosuccinimide (0.15 g, 0.65 mmol). BF3*2H2O (0.47 mL, 7.4 mmol) 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 using EtOAc:Toluene 3:1->7:1 as the eluent to afford N-[1-(5-Iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-isobutyramide as a solid.

Workup

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

Sources & evidence

ORD record
ord-87100de2956d41879bf953c7782766f4
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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