Methyl iodide → HCID 58053580, compound

HRID 524940Notes

Reaction equation

HRID 524940 reaction equation
[H-].[Na+].[I:3][C:4]1[C:5]([O:18][CH3:19])=[CH:6][C:7]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[N:8][CH:9]=1.[CH3:20]I>CN(C=O)C>[I:3][C:4]1[C:5]([O:18][CH3:19])=[CH:6][C:7]([N:10]([CH3:20])[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:15])[CH3:16])=[N:8][CH:9]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 24229210tert-Butyl (5-iodo-4-methoxypyridin-2-yl)carbamate

Product 1

HCID 58053580HCID 58053580, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (37.70 mg, 0.9425 mmol) was added to a stirred suspension of tert-butyl N-(5-iodo-4-methoxy-2-pyridyl)carbamate (300 mg, 0.8568 mmol) in DMF (3 mL) and the reaction was stirred at 0° C. for 15 minutes. MeI (145.9 mg, 63.99 μL, 1.028 mmol) was added and the reaction allowed to warm to ambient temperature over 1 hour. The mixture was quenched by the addition of water, diluted with EtOAc and the layers separated. The organic layer washed with saturated aqueous NaHCO3 (×1), brine (×2), dried (MgSO4) filtered and concentrated in vacuo. The residue was purified by column chromatography (ISCO Companion, 40 g column, eluting with 0 to 30% EtOAc/Petroleum Ether, loaded in DCM) to give tert-butyl (5-iodo-4-methoxypyridin-2-yl)(methyl)carbamate as a colourless oil (269 mg, 86% Yield). MS (ES+-t-Bu) 309.4.

Workup

  1. temperatureto warm to ambient temperature over 1 hour
  2. customThe mixture was quenched by the addition of water
  3. additiondiluted with EtOAc
  4. customthe layers separated
  5. washThe organic layer washed with saturated aqueous NaHCO3 (×1), brine (×2)
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by column chromatography (ISCO Companion, 40 g column, eluting with 0 to 30% EtOAc/Petroleum Ether, loaded in DCM)

Sources & evidence

ORD record
ord-ddabc72866b24b6fa947df9081386a10
Source dataset
uspto-grants-2016_05
Patent number
US09340546B2

Reaction notes

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