Sodium Thiosulfate → HCID 58074581, compound

HRID 1848343Notes

Reaction equation

HRID 1848343 reaction equation
[CH3:1][O:2][C:3]1[C:4]2[N:5]([N:9]=[C:10]([C:12]3([CH2:15][OH:16])[CH2:14][CH2:13]3)[N:11]=2)[CH:6]=[CH:7][CH:8]=1.[I:17]N1C(=O)CCC1=O.B(F)(F)F.O.O.C([O-])(O)=O.[Na+].[O-]S([O-])(=S)=O.[Na+].[Na+]>>[I:17][C:6]1[N:5]2[N:9]=[C:10]([C:12]3([CH2:15][OH:16])[CH2:14][CH2:13]3)[N:11]=[C:4]2[C:3]([O:2][CH3:1])=[CH:8][CH:7]=1

Participants

6

Reactant 5

HCID 24477Sodium ThiosulfateHCID 61591Boron trifluoride dihydrateHCID 120273N-IodosuccinimideHCID 516892Sodium BicarbonateHCID 66707624HCID 66707624, compound

Product 1

HCID 58074581HCID 58074581, compoundYield 52.3%

Procedure

A mixture of (1-(8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropyl)methanol (1.7 g, 7.76 mmol) and N-iodosuccinimide (1.7 g, 7.76 mmol) was treated with BF3.2H2O (8.5 g, 77.6 mmol, 5.3 ml) at RT. After 24 h, the reaction mixture was poured into a 1:1 mixture of the aq. solutions of NaHCO3 (1 M) and Na2S2O3 (1 M) and extracted with DCM. The combined organic phase was washed with H2O, over anhyd. Na2SO4 and concentrated under reduced pressure. The residue obtained was purified by column chromatography to afford (1-(5-iodo-8-methoxy-[1,2,4]triazolo[1,5-a]pyridin-2-yl)cyclopropyl)methanol (1.4 g, 52%) as a solid.

Workup

  1. extractionextracted with DCM
  2. washThe combined organic phase was washed with H2O
  3. concentrationNa2SO4 and concentrated under reduced pressure
  4. customThe residue obtained
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-e352c52beaa84816a1c6c3389129fbea
Source dataset
uspto-grants-2015_02
Patent number
US08952162B2

Reaction notes

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