N-Iodosuccinimide → HCID 178517802, compound

HRID 1854721Notes

Reaction equation

HRID 1854721 reaction equation
C1C(=O)N([I:8])C(=O)C1.[Br:9][C:10]1[CH:11]=[CH:12][C:13]([OH:17])=[N:14][C:15]=1[Cl:16]>CO>[Br:9][C:10]1[CH:11]=[C:12]([I:8])[C:13]([OH:17])=[N:14][C:15]=1[Cl:16]

Participants

4

Reactant 2

HCID 120273N-IodosuccinimideHCID 178515816HCID 178515816, compound

Product 1

HCID 178517802HCID 178517802, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
45 °C

Procedure

NIS (7.38 g, 32.8 mmol) was added to a stirring solution of commercially available 5-bromo-6-chloropyridin-2-ol (5.70 g, 27.3 mmol) in MeOH (50 ml) at 45° C. The reaction was allowed to stir at 45° C. for 1 h. The amber colored solution was cooled to rt and then concentrated in vacuo. The resulting yellow solids were diluted with 25 mL DCM, triturated for 30 min, then collected filtering with minimal DCM to give 5-bromo-6-chloro-3-iodopyridin-2-ol (7.60 g, 22.7 mmol, 83% yield) as a white solid consistent by LCMS and NMR. LCMS: m/e 335 (M+H)+ LCMS retention time: 2.62 min. (Column: Phenomenex-Luna 50×2.0 mm 3u. Solvent A=90% Water: 10% Methanol: 0.1% TFA. Solvent B=10% Water: 90% Methanol: 0.1% TFA. Start % B=0. Final % B=100. Gradient Time=4 min. Flow Rate=0.8 mL/min.). 1H NMR (500 MHz, MeOD) δ ppm 8.26 (s, 1H).

Workup

  1. temperatureThe amber colored solution was cooled to rt
  2. concentrationconcentrated in vacuo
  3. additionThe resulting yellow solids were diluted with 25 mL DCM
  4. customtriturated for 30 min
  5. customcollected
  6. filtrationfiltering with minimal DCM

Sources & evidence

ORD record
ord-7d496d7eb36c491dbe0ec15dc516c484
Source dataset
uspto-grants-2015_02
Patent number
US08962651B2

Reaction notes

Loading…