Methyl iodide → HCID 178503329, compound

HRID 2264217Notes

Reaction equation

HRID 2264217 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH:11]=[C:12]2[NH:24][C:23](=[S:25])[NH:22][C:13]2=[N:14][C:15]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1.I[CH3:27]>CN(C=O)C>[F:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][C:9]=1[C:10]1[CH:11]=[C:12]2[N:24]=[C:23]([S:25][CH3:27])[NH:22][C:13]2=[N:14][C:15]=1[C:16]1[CH:17]=[N:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86624406HCID 86624406, compound

Product 1

HCID 178503329HCID 178503329, compoundYield 54.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Conditions

Temperature
0 °C

Procedure

To a suspension of sodium hydride 60% (0.098 g, 2.45 mmols) in DMF (5 mL) a suspension of 6-(3-fluoropyridin-4-yl)-5-pyridin-3-yl-1,3-dihydro-2H-imidazo[4,5-b]pyridine-2-thione (0.6 g, 1.86 mmols) in DMF (15 mL) was added dropwise, at 0° C., under argon. The solution was allowed to stir for 30 minutes at 0° C. and then iodomethane (0.116 mL, 1.86 mmol) in DMF (1 mL) was added dropwise. The reaction mixture was warmed up to room temperature and stirred for 2.5 hours. The mixture was concentrated and purified by silica gel flash chromatography (150:40:5 dichloromethane/methanol/ammonia) to give the title compound (0.34 g, 54% of yield).

Workup

  1. additionwas added dropwise, at 0° C., under argon
  2. temperatureThe reaction mixture was warmed up to room temperature
  3. stirringstirred for 2.5 hours
  4. concentrationThe mixture was concentrated
  5. custompurified by silica gel flash chromatography (150:40:5 dichloromethane/methanol/ammonia)

Sources & evidence

ORD record
ord-1c189ef0a54349fb80ec1eb491e02b18
Source dataset
uspto-grants-2010_12
Patent number
US07855202B2

Reaction notes

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