Isopropanol → 4-Iodo-2-isopropoxypyridine

HRID 76128Notes

Reaction equation

HRID 76128 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][NH:5][C:4](=[O:8])[CH:3]=1.[CH3:9][CH:10](O)[CH3:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([O:8][CH:10]([CH3:11])[CH3:9])[CH:3]=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

Conditions

Temperature
0 °C

Procedure

To 2.30 g (10.4 mmol) 4-iodo-1H-pyridin-2-one in 130 mL DCM are added 0.88 mL (11.4 mmol) 2-propanol and 3.00 (11.4 mmol) triphenylphosphine. After cooling down to 0° C. 2.23 mL (11.4 mmol) DIAD are added dropwise. After 5 min the cooling is removed and the mixture is stirred at r.t. for 2 h. The reaction mixture is washed with water and brine, dried with Na2SO4 and the solvent is removed in vacuo. The crude product is purified by column chromatography (silica gel, heptane/EtOAc 90/10).

Workup

  1. customAfter 5 min the cooling is removed
  2. washThe reaction mixture is washed with water and brine
  3. dry with materialdried with Na2SO4
  4. customthe solvent is removed in vacuo
  5. customThe crude product is purified by column chromatography (silica gel, heptane/EtOAc 90/10)

Sources & evidence

ORD record
ord-a7ee215bd57a4055a728196eeb8cfebe
Source dataset
uspto-grants-2014_09
Patent number
US08835472B2

Reaction notes

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