Water → 2-Iodo-3-methoxypyridine

HRID 1028569Notes

Reaction equation

HRID 1028569 reaction equation
[I:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]([O-])([O-])=O.[Cs+].[Cs+].CI.O>CN(C=O)C.CCOC(C)=O>[I:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 971792-Iodopyridin-3-ol

Product 1

HCID 8171732-Iodo-3-methoxypyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-iodopyridin-3-ol (45.3 mg, 0.205 mmol) in DMF (3 mL) was added Cs2CO3 (334 mg, 1.030 mmol) and MeI (25 μL, 0.410 mmol). After 1 hour, the reaction was poured into water (10 mL), diluted with EtOAc (20 mL), washed with water (3×10 mL) and brine (10 mL). The organic layer was dried over Na2SO4, filtered, and concentrated to afford 2-iodo-3-methoxypyridine. LCMS=236.1 (M+1)+. 1H NMR (CDCl3, 500 MHz) δ 8.00 (dd, J=1.4, 4.6 Hz, 1H), 7.20 (dd, J=4.6, 8.0 Hz, 1H), 7.00 (dd, 1.4, 8.3 Hz, 1H), 3.90 (s, 3H).

Workup

  1. washwashed with water (3×10 mL) and brine (10 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-2196d8bc79dd49668081edd5e8706276
Source dataset
uspto-grants-2014_05
Patent number
US08735435B2

Reaction notes

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