Nitrogen → 2-Methyl-3-trichloroacetyl-7-methoxyindole

HRID 480574

Reaction equation

HRID 480574 reaction equation
N#N.[CH3:3][C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][C:7]=2[O:13][CH3:14].N1C(C)=CC(C)=CC=1C.[Cl:24][C:25]([Cl:30])([Cl:29])[C:26](Cl)=[O:27]>C(#N)C>[CH3:3][C:4]1[NH:5][C:6]2[C:11]([C:12]=1[C:26](=[O:27])[C:25]([Cl:30])([Cl:29])[Cl:24])=[CH:10][CH:9]=[CH:8][C:7]=2[O:13][CH3:14]

Participants

6

Reactant 4

HCID 947NitrogenHCID 6420Trichloroacetyl chlorideHCID 79532,4,6-TrimethylpyridineHCID 3266147-methoxy-2-methyl-1H-indole

Product 1

HCID 187654172-Methyl-3-trichloroacetyl-7-methoxyindoleYield 100.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a 2 L round-bottomed flask equipped with a magnetic stirrer and a N2 bubbler were added 2-methyl-7-methoxyindole (12 g, 74 mmol), acetonitrile (125 mL) and collidine (15 mL, 113 mmol). The mixture was stirred to give a solution and was cooled with an ice water bath. Trichloroacetyl chloride (14 mL, 112 mmol) was added. The cooling bath was removed and the reaction mixture stirred at RT for 3 h. 1N HCl (500 mL) was then added over 10 minutes. The resulting slurry was stirred at RT for 30 minutes and filtered. The cake was washed with DI water (3×50 mL) and suction dried for 17 h to give 2-methyl-3-trichloroacetyl-7-methoxyindole (22.8 g, 96% yield). 1H NMR (CDCl3) δ2.79 (s, 3H), 3.96 (s, 3H), 6.71 (d, J=7.9 Hz, 1H), 7.19 (dd, J=7.9, 8.4 Hz, 1H), 7.82 (d, J=8.4 Hz, 1H), 8.92 (s, 1H).

Workup

  1. customTo a 2 L round-bottomed flask equipped with a magnetic stirrer
  2. customto give a solution
  3. temperaturewas cooled with an ice water bath
  4. customThe cooling bath was removed
  5. stirringthe reaction mixture stirred at RT for 3 h
  6. addition1N HCl (500 mL) was then added over 10 minutes
  7. stirringThe resulting slurry was stirred at RT for 30 minutes
  8. filtrationfiltered
  9. washThe cake was washed with DI water (3×50 mL) and suction
  10. customdried for 17 h

Sources & evidence

ORD record
ord-e61d8aad82694495aa717ba9557052fe
Source dataset
uspto-grants-2003_11
Patent number
US06653304B2

Linked notes

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