Methyl iodide → HCID 68185023, compound

HRID 2409973Notes

Reaction equation

HRID 2409973 reaction equation
[CH3:1][S:2]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][C:20]([CH3:24])=[CH:21][CH:22]=3)[NH:17][C:16]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:9]=1)=[O:7])(=[O:4])=[O:3].[C:31](=O)([O-])[O-].[Cs+].[Cs+].CI>CN(C)C=O.O>[CH3:1][S:2]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH2:14][C:15]2[C:23]3[C:18](=[CH:19][C:20]([CH3:24])=[CH:21][CH:22]=3)[N:17]([CH3:31])[C:16]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[N:9]=1)=[O:7])(=[O:3])=[O:4]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 60151297HCID 60151297, compound

Product 1

HCID 68185023HCID 68185023, compoundYield 37.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of N-methanesulfonyl-6-(6-methyl-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxamide (100 mg) in N,N-dimethylformamide (1.2 mL) were added cesium carbonate (155 mg) and methyl iodide (0.023 mL), and this mixture was stirred at room temperature for 17 hours. The reaction mixture was diluted with water, followed by extraction with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (38.3 mg). 1H-NMR (DMSO-d6) δ ppm: 2.43 (3H, s), 3.38 (3H, s), 3.57 (3H, s), 4.21 (2H, s), 6.82-6.89 (1H, m), 7.24-7.33 (2H, m), 7.37 (1H, d, J=8.0 Hz), 7.43-7.58 (5H, m), 7.81-7.90 (2H, m), 10.90-11.55 (1H, br). ESI-MS (m/z): 434 (M+H)+.

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-hexane)

Sources & evidence

ORD record
ord-e8ad03eb2776459b865994e0681fcfd1
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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