Water → 3-Iodo-6-isopropoxypyridazine

HRID 330830Notes

Reaction equation

HRID 330830 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].[H-].[Na+].[I:7][C:8]1[N:9]=[N:10][C:11](I)=[CH:12][CH:13]=1.O>C1COCC1>[I:7][C:8]1[N:9]=[N:10][C:11]([O:4][CH:1]([CH3:3])[CH3:2])=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962WaterHCID 3776IsopropanolHCID 24758Sodium hydrideHCID 2503833,6-Diiodopyridazine

Product 1

HCID 218161973-Iodo-6-isopropoxypyridazine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.50 mL (6.6 mmol) isopropanol are added to 289 mg (7.23 mmol) sodium hydride (60%) in 100 mL THF and the mixture is stirred for 30 min at rt. After that time, 2.0 g (6.0 mmol) 3,6-diiodo-pyridazine are added and the mixture is stirred for 14 h at rt and for 14 h at 50° C. After that time, the mixture is poured into water and extracted with EtOAc. The organic layer is washed with water (2×) and dried over sodium sulphate. The solvent is removed in vacuo and the residue is purified by column chromatography (silicia gel; heptane:EtOAc gradient 0 to 50%).

Workup

  1. stirringthe mixture is stirred for 14 h at rt and for 14 h at 50° C
  2. extractionextracted with EtOAc
  3. washThe organic layer is washed with water (2×)
  4. dry with materialdried over sodium sulphate
  5. customThe solvent is removed in vacuo
  6. customthe residue is purified by column chromatography (silicia gel; heptane:EtOAc gradient 0 to 50%)

Sources & evidence

ORD record
ord-0f1670aedab349a8a7a3fbb64f042d99
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

Loading…