Methanol → 4-Iodo-2-methoxypyridine

HRID 1361646Notes

Reaction equation

HRID 1361646 reaction equation
F[C:2]1[CH:7]=[C:6]([I:8])[CH:5]=[CH:4][N:3]=1.[C:9](=O)([O-])[O-:10].[Cs+].[Cs+].C1COCC1.CO>O>[I:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([O:10][CH3:9])[CH:7]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 10796Cesium carbonateHCID 70235702-Fluoro-4-iodopyridine

Product 1

HCID 150197954-Iodo-2-methoxypyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

To 2-fluoro-4-iodopyridine (500 mg, 2.2 mmol) and cesium carbonate (730 mg, 2.2 mmol) was added THF (5 mL) and MeOH (0.091 mL, 2.2 mmol). The resulting mixture was heated to 50° C. for 24 hours in a sealed tube. The cooled mixture was diluted with water and extracted with EtOAc. The organic layer was dried over sodium sulfate, filtered and concentrated to yield the title compound. MS m/z=236 [M+1]+. Calc'd for C6H61NO: 235.03.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-341fc7ada29748298b53b664c4501f56
Source dataset
uspto-grants-2011_02
Patent number
US07880000B2

Reaction notes

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