Methyl iodide → HCID 55141659, compound

HRID 1431351Notes

Reaction equation

HRID 1431351 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([NH:8][CH2:9][CH2:10][CH2:11][O:12][CH3:13])=[N:6][CH:7]=1.[H-].[Na+].I[CH3:20]>CN(C=O)C.O>[Br:1][C:2]1[CH:3]=[C:4]([N+:14]([O-:16])=[O:15])[C:5]([N:8]([CH2:9][CH2:10][CH2:11][O:12][CH3:13])[CH3:20])=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 59631510HCID 59631510, compound

Product 1

HCID 55141659HCID 55141659, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A dry round bottom flask containing 5-bromo-N-(3-methoxypropyl)-3-nitropyridin-2-amine (1.0 g, 3.45 mmol) in dry DMF (4.5 mL) was cooled to 0° C., then sodium hydride, 60% dispersion in mineral oil (0.28 g, 7.02 mmol) was added carefully in portions. The mixture was stirred at 0° C. for 15 min, then iodomethane (0.66 mL, 10.6 mmol) was added dropwise. Upon complete addition, the mixture was allowed to warm to 23° C. After 19 h, the reaction was carefully diluted with water then extracted five times with EtOAc. The organic extraction was then washed one time with brine and dried over anhydrous magnesium sulfate. After filtration and concentration, the residue was purified on silica gel (0-25% EtOAc in hexanes) to afford a light yellow oil as 5-bromo-N-(3-methoxy propyl)-N-methyl-3-nitropyridin-2-amine. 1H NMR (400 MHz, CDCl3) δ ppm 8.31 (1H, d, J=2.3 Hz), 8.21 (1H, d, J=2.3 Hz), 3.79 (2H, m), 3.47 (2H, m), 3.33 (3H, s), 2.86 (3H, s), 2.01 (2H, m).

Workup

  1. additionUpon complete addition
  2. temperatureto warm to 23° C
  3. waitAfter 19 h
  4. extractionthen extracted five times with EtOAc
  5. extractionThe organic extraction
  6. washwas then washed one time with brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. filtrationAfter filtration and concentration
  9. customthe residue was purified on silica gel (0-25% EtOAc in hexanes)

Sources & evidence

ORD record
ord-95664f3c27934783902897f26cd5cabb
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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