Methyl iodide → HCID 118022858, compound

HRID 518325Notes

Reaction equation

HRID 518325 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1.[H-].[Na+].[CH3:20]I>CN(C=O)C>[Br:1][C:2]1[CH:3]=[C:4]([N:10]([CH3:20])[C:11](=[O:17])[O:12][C:13]([CH3:14])([CH3:16])[CH3:15])[C:5](=[O:9])[N:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 118022092HCID 118022092, compound

Product 1

HCID 118022858HCID 118022858, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl N-(5-bromo-1-methyl-2-oxopyridin-3-yl)carbamate (150.0 mg, impure) in DMF (10 mL) was added NaH (60.0 mg, 1.5 mol, 60% in oil) in portions at 0° C. It was stirred for 30 min. Then CH3I (231.0 mg, 1.5 mmol) was added dropwise at 0° C. The reaction mixture was stirred for 2 h at 30° C. The reaction was quenched with saturated aqueous NH4Cl (15 mL), extracted with EA (20 mL), washed with brine (20 mL), dried over Na2SO4, filtered and concentrated to give the title compound (120.0 mg, crude) as a green solid, which was used directly in the next step without purification.

Workup

  1. stirringThe reaction mixture was stirred for 2 h at 30° C
  2. customThe reaction was quenched with saturated aqueous NH4Cl (15 mL)
  3. extractionextracted with EA (20 mL)
  4. washwashed with brine (20 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bce5bdf9b06d433daf60abe69d5ae6a6
Source dataset
uspto-grants-2015_08
Patent number
US09115114B2

Reaction notes

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