Methyl iodide → HCID 66764944, compound

HRID 1466764Notes

Reaction equation

HRID 1466764 reaction equation
[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[NH:13][C:12]=2[CH3:21])[CH:5]=1.[CH3:23][Si]([N-][Si](C)(C)C)(C)C.[Li+].IC>CN(C=O)C.C1COCC1>[CH3:1][O:2][C:3](=[O:22])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([S:10][C:11]2[C:19]3[C:14](=[CH:15][C:16]([Cl:20])=[CH:17][CH:18]=3)[N:13]([CH3:23])[C:12]=2[CH3:21])[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 66765016HCID 66765016, compound

Product 1

HCID 66764944HCID 66764944, compound

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Conditions

Temperature
-78 °C

Procedure

3-(6-Chloro-2-methyl-1H-indol-3-ylsulfanyl)-benzoic acid methyl ester (0.0752 g, 0.23 mmol) was dissolved in DMF:THF (1:1, 4 mL) and cooled to −78° C. Lithium bis(trimethylsilyl)amide solution (0.500 mL, 0.5 mmol, 1.0M in hexanes) was added. After 1 hour, iodomethane (11 μL, 0.18 mmol) was added and the reaction was allowed to warm to room temperature over 30 minutes then submitted to aqueous workup. Purification by silica gel chromatography (0-100% EtOAc in hexanes) provided the title compound.

Workup

  1. temperatureto warm to room temperature over 30 minutes
  2. customPurification by silica gel chromatography (0-100% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8573ced97ca04b94b4671b512104fea3
Source dataset
uspto-grants-2015_04
Patent number
US09000025B2

Reaction notes

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