Boron trifluoride → HCID 86661598, compound

HRID 1848356Notes

Reaction equation

HRID 1848356 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]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[O:18])[CH2:14][CH2:13]3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1.[I:24]N1C(=O)CCC1=O.B(F)(F)F.[O-]S([O-])(=S)=O.[Na+].[Na+]>C([O-])(O)=O.[Na+]>[I:24][C:6]1[N:5]2[N:9]=[C:10]([C:12]3([CH2:15][NH:16][C:17]([N:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[O:18])[CH2:14][CH2:13]3)[N:11]=[C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 6356Boron trifluoride2×HCID 24477Sodium ThiosulfateHCID 120273N-Iodosuccinimide2×HCID 66707623HCID 66707623, compound

Product 1

HCID 86661598HCID 86661598, compound

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

Under an argon atmosphere Pyrrolidine-1-carboxylic acid [1-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-amide (0.085 g, 0.23 mmol) was mixed with N-iodosuccinimide (0.16 g, 0.69 mmol). BF3*2H2O (0.5 mL, 7.8 mmol) was added at 0° C. The dark suspension was stirred at rt for 4 h after which N-iodosuccinimide (0.08 g1) and BF3*2H2O (0.25 mLl) were added. The suspension was stirred for 24 h all together after which it was poured onto a 1:1 solution of saturated Na2S2O3 and saturated NaHCO3 (30 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 DCM:MeOH 97:3 as the eluent to afford Pyrrolidine-1-carboxylic acid [1-(5-iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)-cyclopropylmethyl]-amide.

Workup

  1. additionwere added
  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-e07c7c0fabf04a8d8c7ccda6f6405ff0
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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