Methyl iodide → [5-(1H-Indol-2-yl)-2-methoxy-phenyl]-methyl-amine

HRID 25516

Reaction equation

HRID 25516 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([O:17][CH3:18])=[C:14]([NH2:16])[CH:15]=1.[C:19](=O)([O-])[O-].[K+].[K+].CI>CC(C)=O>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]1[CH:11]=[CH:12][C:13]([O:17][CH3:18])=[C:14]([NH:16][CH3:19])[CH:15]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 99002045-(1H-indol-2-yl)-2-methoxy-phenylamine

Product 1

HCID 9921288[5-(1H-Indol-2-yl)-2-methoxy-phenyl]-methyl-amineYield 27%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
40 °C

Procedure

In acetone (50 mL) was placed 5-(1H-indol-2-yl)-2-methoxy-phenylamine (2.38 g, 10 mmol). To this was added potassium carbonate (5.53 g, 40 mmol), and to the vigorously stirred mixture was added methyl iodide (1.55 g, 11 mmol). The mixture warmed to 40° C. and stirred for 48 hours. The mixture cooled to room temperature and was filtered free of inorganics. The resulting solution was evaporated in vacuo to give a solid which was partitioned between ethyl acetate (50 mL) and water (50 mL). The organic phase was separated, dried over magnesium sulfate, and evaporated in vacuo to give a tan solid. This solid was purified by flash chromatography over silica gel (5% ethyl acetate/methylene chloride). Evaporation of the appropriate fractions gave 0.68 g of pure compound. MS: M+1=253.1. 1H NMR (DMSO-d6) δ 2.79 (d, J=5.3 Hz, 3H), 3.80 (s, 3H), 5.08-5.12 (m, 1H), 6.69 (s, 1H), 6.83-7.05 (m, 5H), 7.33 (d, J=7.9 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 11.28 (s, 1H) ppm.

Workup

  1. temperatureThe mixture cooled to room temperature
  2. filtrationwas filtered free of inorganics
  3. customThe resulting solution was evaporated in vacuo
  4. customto give a solid which
  5. customwas partitioned between ethyl acetate (50 mL) and water (50 mL)
  6. customThe organic phase was separated
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customto give a tan solid
  10. customThis solid was purified by flash chromatography over silica gel (5% ethyl acetate/methylene chloride)
  11. customEvaporation of the appropriate fractions

Sources & evidence

ORD record
ord-5c508525b84f40e6abab25c56de6090c
Source dataset
uspto-grants-2005_02
Patent number
US06858739B2

Linked notes

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