Methyl iodide → HCID 66738428, compound

HRID 1640911Notes

Reaction equation

HRID 1640911 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:21])[NH:9][CH2:10][CH2:11][O:12][C:13]1[CH:14]=[N:15][C:16]([F:20])=[CH:17][C:18]=1[I:19])([CH3:6])([CH3:5])[CH3:4].[CH3:22]I>CN(C=O)C>[C:3]([O:7][C:8](=[O:21])[N:9]([CH2:10][CH2:11][O:12][C:13]1[CH:14]=[N:15][C:16]([F:20])=[CH:17][C:18]=1[I:19])[CH3:22])([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 66738123HCID 66738123, compound

Product 1

HCID 66738428HCID 66738428, compoundYield 38.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (620 mg, 26 mmol) to a solution of [2-(6-fluoro-4-iodo-pyridin-3-yloxy)-ethyl]-carbamic acid tert-butyl ester (0.33 g, 0.86 mmol) in 3 mL of DMF. Stir the mixture at RT for 1 h and add methyl iodide (0.37 g, 2.59 mmol). Stir the reaction mixture at RT overnight. Add water and extract with ethyl acetate. Wash the organic layer with saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo. Purify the residue by column chromatography (20% ethyl acetate in hexane) to afford the title compound as a light yellow solid (0.13 g, 38%). 1H NMR (400 MHz, CD3CN) δ 1.45 (s, 9H), 3.08 (s, 3H), 3.59 (t, J=5.6 Hz, 2H), 4.20 (t, J=5.6 Hz, 2H), 5.07 (s, 1H), 7.38 (d, J=3.2 Hz, 1H), 7.61 (d, J=1.2 Hz, 1H).

Workup

  1. stirringStir the reaction mixture at RT overnight
  2. extractionAdd water and extract with ethyl acetate
  3. washWash the organic layer with saturated aqueous sodium chloride
  4. dry with materialDry the mixture over sodium sulfate
  5. concentrationConcentrate the solution in vacuo
  6. customPurify the residue by column chromatography (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-b8797ef8388e42a19427f5c6ba0d42f4
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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