Methyl iodide → HCID 57675751, compound

HRID 1092427Notes

Reaction equation

HRID 1092427 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH2:26][OH:27])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:29]>C(#N)C.[Ag-]=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:23]3[C:18](=[CH:19][C:20]([O:24][CH3:25])=[CH:21][CH:22]=3)[CH:17]=[C:16]2[CH2:26][O:27][CH3:29])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 57675741HCID 57675741, compound

Product 1

HCID 57675751HCID 57675751, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 178418778HCID 178418778, compoundCatalystHCID 6342AcetonitrileSolvent

Conditions

Temperature
40 °C

Procedure

[1-(4-Benzyloxyphenyl)-5-methoxy-1H-indol-2-yl]methanol (0.2 g, 0.56 mmol) was dissolved in acetonitrile (2 mL), and iodomethane (0.35 mL, 5.6 mmol) and silver(I) oxide (0.39 g, 1.68 mmol) were added. The mixture was stirred overnight at 40° C., then cooled to room temperature and filtered through a pad of Celite. The filtrate was concentrated. SiO2 chromatography with 3-50% ethyl acetate/hexanes gave 0.16 g (77% yield) of the desired product. LC-MS (C24H23NO3 calc'd 373) m/z 374 (M+H).

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered through a pad of Celite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b779a41929194a2caea01c4e14d5bf9e
Source dataset
uspto-grants-2012_03
Patent number
US08129424B2

Reaction notes

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