Methyl iodide → N-(cyclopropylmethyl)-2-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-N-methyl-4-(methylsulfonyl)aniline

HRID 633540Notes

Reaction equation

HRID 633540 reaction equation
[CH:1]1([CH2:4][NH:5][C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:16]2[C:24]3[C:19](=[C:20]([O:25][CH3:26])[N:21]=[CH:22][CH:23]=3)[N:18]([CH3:27])[CH:17]=2)[CH2:3][CH2:2]1.[H-].[Na+].I[CH3:31]>CN(C)C=O>[CH:1]1([CH2:4][N:5]([CH3:31])[C:6]2[CH:11]=[CH:10][C:9]([S:12]([CH3:15])(=[O:14])=[O:13])=[CH:8][C:7]=2[C:16]2[C:24]3[C:19](=[C:20]([O:25][CH3:26])[N:21]=[CH:22][CH:23]=3)[N:18]([CH3:27])[CH:17]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 90387888N-(cyclopropylmethyl)-2-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-4-(methylsulfonyl)aniline

Product 1

HCID 90416403N-(cyclopropylmethyl)-2-(7-methoxy-1-methyl-1H-pyrrolo[2,3-c]pyridin-3-yl)-N-methyl-4-(methylsulfonyl)anilineYield 100%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of the product from Example 44B (0.116 g, 0.301 mmol) in dimethylformamide (2 mL) under nitrogen was treated with sodium hydride (0.018 g, 0.451 mmol) at ambient temperature, stirred for 30 minutes, treated with iodomethane (0.038 mL, 0.602 mmol), stirred for 30 minutes at ambient temperature and quenched into cold water. The mixture was extracted into ethyl acetate and the organic layer was washed with saturated aqueous sodium chloride, dried (anhydrous Na2SO4), filtered, and concentrated to afford the title compound (0.12 g, 100%).

Workup

  1. stirringstirred for 30 minutes at ambient temperature
  2. customquenched into cold water
  3. extractionThe mixture was extracted into ethyl acetate
  4. washthe organic layer was washed with saturated aqueous sodium chloride
  5. dry with materialdried (anhydrous Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-4f77fa95dce449dfa5cfcff1582818bb
Source dataset
uspto-grants-2016_04
Patent number
US09321764B2

Reaction notes

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