Isopropanol → 4-Iodo-2-isopropoxypyridine

HRID 330838Notes

Reaction equation

HRID 330838 reaction equation
[CH3:1][CH:2]([OH:4])[CH3:3].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[I:24][C:25]1[CH:30]=[CH:29][NH:28][C:27](=O)[CH:26]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[I:24][C:25]1[CH:30]=[CH:29][N:28]=[C:27]([O:4][CH:2]([CH3:3])[CH3:1])[CH:26]=1

Participants

6

Reactant 4

HCID 3776IsopropanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 205825354-Iodo-1,2-dihydropyridin-2-one

Product 1

HCID 666140134-Iodo-2-isopropoxypyridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.88 mL (11.4 mmol) 2-propanol and 3.00 (11.4 mmol) triphenylphosphine are added to 2.30 g (10.4 mmol) 4-iodo-1H-pyridin-2-one (XXI.1) in 130 mL DCM. Finally, 2.23 mL (11.4 mmol) DIAD are added at 0° C. After 5 min stirring, cooling is suspended and the mixture is stirred at rt for 2 h. After that time, the mixture is washed with water and brine, dried over sodium sulphate and the solvent is removed in vacuo. The crude product is purified by column chromatography (silicia gel; heptane/EtOAc 90/10).

Workup

  1. temperaturecooling
  2. stirringthe mixture is stirred at rt for 2 h
  3. washAfter that time, the mixture is washed with water and brine
  4. dry with materialdried over sodium sulphate
  5. customthe solvent is removed in vacuo
  6. customThe crude product is purified by column chromatography (silicia gel; heptane/EtOAc 90/10)

Sources & evidence

ORD record
ord-723a4859feb6422d875bb23497aac712
Source dataset
uspto-grants-2014_11
Patent number
US08877754B2

Reaction notes

Loading…