Dimethylformamide → Methyl 3-methoxypyridine-2-carboxylate

HRID 341484Notes

Reaction equation

HRID 341484 reaction equation
[OH:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1.[C:12](=O)([O-])[O-].[K+].[K+].IC.CN(C=O)C>O>[CH3:12][O:1][C:2]1[C:3]([C:8]([O:10][CH3:11])=[O:9])=[N:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 819341Methyl 3-Hydroxy-2-pyridinecarboxylate2×

Product 1

HCID 20474189Methyl 3-methoxypyridine-2-carboxylateYield 45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 3-hydroxypyridine-2-carboxylate (Intermediate 96, 1.2 g, 7.8 mmol), potassium carbonate (1.2 g, 8.7 mmol), iodomethane (0.63 ml, 1.0 mmol) and DMF (10 ml) was stirred overnight. The mixture was diluted with water (20 ml) and extracted with ethyl acetate (2×20 ml). The combined organic extracts were washed with water and concentrated under vacuum. The residue (0.82 g) was purified by flash column chromatography (5 g silica; heptane-ethyl acetate, 1:0-5:1-2:1) to give the title compound as a clear oil (0.58 g, 45%). Method C HPLC-MS: MH+ requires m/z=168. Found: m/z=168, Rt=0.76 min (100%).

Workup

  1. extractionextracted with ethyl acetate (2×20 ml)
  2. washThe combined organic extracts were washed with water
  3. concentrationconcentrated under vacuum
  4. customThe residue (0.82 g) was purified by flash column chromatography (5 g silica; heptane-ethyl acetate, 1:0-5:1-2:1)

Sources & evidence

ORD record
ord-e80ac57eeb7646c29b92b8f930960504
Source dataset
uspto-grants-2014_11
Patent number
US08895733B2

Reaction notes

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