Methyl iodide → Cyclohexyl(1-methyl-1H-pyrrol-2-yl)methanone

HRID 1844735Notes

Reaction equation

HRID 1844735 reaction equation
[CH:1]1([C:7]([C:9]2[NH:10][CH:11]=[CH:12][CH:13]=2)=[O:8])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:16]I>CN(C=O)C>[CH:1]1([C:7]([C:9]2[N:10]([CH3:16])[CH:11]=[CH:12][CH:13]=2)=[O:8])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 13432026Cyclohexyl(1H-pyrrol-2-yl)methanone

Product 1

HCID 14043405Cyclohexyl(1-methyl-1H-pyrrol-2-yl)methanoneYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 25a (2.0 g, 11.3 mmol dissolved dry DMF) was added portionwise to the mixture of NaH (60%; 0.904 g, 22.6 mmol) and dry DMF (200 mL) and the mixture was stirred for 30 min at rt, then MeI (1.9 g, 11.6 mmol) was added at 0° C. The stirred mixture was allowed to stand at rt for 2 h, poured slowly into ice-water and extracted with EA. The organic phase was dried (MgSO4), evaporated and purified by CC to give compound 25b (1.73 g, 80%).

Workup

  1. waitto stand at rt for 2 h
  2. extractionextracted with EA
  3. dry with materialThe organic phase was dried (MgSO4)
  4. customevaporated
  5. custompurified by CC

Sources & evidence

ORD record
ord-9d8b94d06ea343abb998c87073ac973e
Source dataset
uspto-grants-2015_02
Patent number
US08946446B2

Reaction notes

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