Methyl iodide → HCID 11544946, compound

HRID 1791405Notes

Reaction equation

HRID 1791405 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[S:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[CH:12][C:11]([O:22][CH3:23])=[C:10]([O:24][CH3:25])[CH:9]=2)=[O:5])[CH3:2].[H-].[Na+].IC.[C:30]1(S)C=CC=CC=1>C(OCC)(=O)C.CN(C)C=O.O1CCCC1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([C:14]=1[S:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:12][C:11]([O:22][CH3:23])=[C:10]([O:24][CH3:25])[CH:9]=2)=[O:5])[CH3:2].[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH3:30])[C:8]2[C:13]([C:14]=1[S:15][C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1)=[CH:12][C:11]([O:22][CH3:23])=[C:10]([O:24][CH3:25])[CH:9]=2)=[O:5])[CH3:2]

Participants

9

Reactant 4

HCID 6328Methyl iodideHCID 7969ThiophenolHCID 24758Sodium hydrideHCID 11544946HCID 11544946, compound

Product 2

HCID 11544946HCID 11544946, compoundHCID 67550091HCID 67550091, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a 0° C. tetrahydrofuran solution of 5,6-dimethoxy-3-phenylsulfanyl-1H-indole-2-carboxylic acid ethyl ester (0.500 g, 1.40 mmol) was added sodium hydride (95%, 0.037 g, 1.54 mmol) followed by iodomethane (0.096 mL, 1.54 mmol). 5,6-dimethoxy-3-phenylsulfanyl-1H-indole-2-carboxylic acid ethyl ester was synthesized in a manner analogous to Intermediate 1, using benzene thiol instead of 2-methyl benzenethiol. N,N-Dimethylformamide was added to homogenize the reaction. The reaction was allowed to warm to room temperature and stir overnight. The reaction was diluted with ethyl acetate (100 mL). The organic layers were washed with 1N hydrochloric acid (25 mL) and brine (25 mL), dried over magnesium sulfate, filtered and concentrated under reduced pressure to yield the title product, which was used without further purification.

Workup

  1. customthe reaction
  2. stirringstir overnight
  3. washThe organic layers were washed with 1N hydrochloric acid (25 mL) and brine (25 mL)
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-eb5d94843e66410cb44db9aeca8b6b7b
Source dataset
uspto-grants-2006_07
Patent number
US07074814B2

Reaction notes

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