Water → HCID 22391185, compound

HRID 1072235Notes

Reaction equation

HRID 1072235 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=3[O:18][CH3:19])[CH:13]=[O:14])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[H-].[Na+].[CH3:22]I.O>CN(C=O)C>[CH3:22][N:1]1[C:9]2[C:4](=[CH:5][C:6]([C:10]3[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=3[O:18][CH3:19])[CH:13]=[O:14])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 223915143-(Indol-5-yl)-4-methoxybenzaldehyde

Product 1

HCID 22391185HCID 22391185, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 3-(indol-5-yl)-4-methoxybenzaldehyde (0.50 g, 2.0 mmol) in DMF (10 mL) was cooled to 0° C. and NaH (60% dispersion in mineral oil, 0.14 g, 3.0 mmol) was added. The mixture was stirred at 0° C. for 45 minutes, then methyl iodide (0.34 g, 4.4 mmol) was added and the reaction was stirred for 16 hours at room temperature. The mixture was then poured into water and extracted with ethyl acetate, washed with water and dried over sodium sulphate. The solvent was removed in vacuo and the crude was purified by column chromatography (hexane/ethyl acetate 7/3) to give 0.48 g of title compound.

Workup

  1. stirringthe reaction was stirred for 16 hours at room temperature
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over sodium sulphate
  5. customThe solvent was removed in vacuo
  6. customthe crude was purified by column chromatography (hexane/ethyl acetate 7/3)

Sources & evidence

ORD record
ord-f052db837bbc425f90662ba2ddf66990
Source dataset
uspto-grants-2005_06
Patent number
US06908935B2

Reaction notes

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