Dimethylformamide → 2-Iodo-3-(4-methoxy-benzyloxy)-pyridine

HRID 2275278Notes

Reaction equation

HRID 2275278 reaction equation
[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[K+].[K+].CN(C=O)C.[CH3:20][O:21][C:22]1[CH:29]=[CH:28][C:25]([CH2:26]Cl)=[CH:24][CH:23]=1>O>[I:1][C:2]1[C:7]([O:8][CH2:26][C:25]2[CH:28]=[CH:29][C:22]([O:21][CH3:20])=[CH:23][CH:24]=2)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 699934-Methyloxybenzyl chlorideHCID 971792-Iodopyridin-3-ol

Product 1

HCID 866638312-Iodo-3-(4-methoxy-benzyloxy)-pyridineYield 27.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
45 °C

Procedure

2-Iodo-pyridin-3-ol (50 mg, 0.226 mmol), K2CO3 (62 mg, 0.452 mmol) and DMF (2 ml) were added with para-methoxybenzyl chloride (46 μL, 0.339 mmol), and the mixture was stirred overnight at 45° C. The resultant was added with water, and then extracted with ethyl acetate. The organic layer was washed with saturated brine, and the resulting residues obtained after concentration under reduced pressure were purified by silica gel column (ethyl acetate/hexane) to obtain the title compound (21 mg, 27%).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customthe resulting residues obtained
  4. concentrationafter concentration under reduced pressure
  5. customwere purified by silica gel column (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-33b0a627b692453bb12a89881809f86c
Source dataset
uspto-grants-2015_09
Patent number
US09126931B2

Reaction notes

Loading…