Methyl iodide → HCID 57675751, compound

HRID 491043Notes

Reaction equation

HRID 491043 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-b345facb0a414f17ac997995919cb04b
Source dataset
uspto-grants-2009_05
Patent number
US07528262B2

Reaction notes

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