Methyl iodide → HCID 68939176, compound

HRID 2377138Notes

Reaction equation

HRID 2377138 reaction equation
[OH-].[K+].[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]([C:15]2[CH:23]=[C:22]3[C:18]([CH:19]=[CH:20][NH:21]3)=[CH:17][CH:16]=2)=[O:14])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1.I[CH3:25]>CN(C=O)C.CCOCC>[CH3:3][O:4][C:5]1[CH:6]=[C:7]([C:13]([C:15]2[CH:23]=[C:22]3[C:18]([CH:19]=[CH:20][N:21]3[CH3:25])=[CH:17][CH:16]=2)=[O:14])[CH:8]=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 68945853HCID 68945853, compound

Product 1

HCID 68939176HCID 68939176, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Potassium hydroxide (0.21 g, 3.7 mmol) was added to a mixture of (3,5-dimethoxy-phenyl)-(1H-indol-6-yl)-methanone (0.69 g, 2.5 mmol) in DMF (7 mL) at 0° C. followed by addtion of iodomethane (0.2 mL, 2.7 mmol) and stirred at 0° C. for 2 hours. The mixture was diluted with ether (15 mL) and washed with brine (2×10 mL). The organic phase was dried over MgSO4, concentrated and purified via flash column chromatography (EtOAc/Hexane) to give (3,5-dimethoxy-phenyl)-(1-methyl-1H-indol-6-yl)-methanone as an off-white solid (0.54 g, 75% yield): 1H NMR (DMSO-d6) δ 3.80 (s, 6H, 20CH3), 3.85 (s, 3H, NCH3), 6.55 (d, J=3 Hz, 1H, Ar), 6.78 (t, J=2 Hz, 1H, Ar), 6.83 (d, J=2 Hz, 2H, Ar), 7.47 (d, J=2 Hz, 1H, Ar), 7.61 (d, J=3 Hz, 1H, Ar), 7.68 (d, J=8 Hz, 1H, Ar), 7.90 (brs, 1H, Ar). The product was used in the next step without further purification.

Workup

  1. washwashed with brine (2×10 mL)
  2. dry with materialThe organic phase was dried over MgSO4
  3. concentrationconcentrated
  4. custompurified via flash column chromatography (EtOAc/Hexane)

Sources & evidence

ORD record
ord-c4be0427097d498198fe24325817a835
Source dataset
uspto-grants-2008_12
Patent number
US07468446B2

Reaction notes

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