Chlorosuccinimide → 7-Chloro-5-methyl-1-tosyl-1H-indol-4-amine

HRID 2174046Notes

Reaction equation

HRID 2174046 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[CH:5][C:4]=2[C:3]=1[NH2:21].C1C(=O)N([Cl:29])C(=O)C1>C(#N)C>[Cl:29][C:9]1[C:8]2[N:7]([S:11]([C:14]3[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=3)(=[O:13])=[O:12])[CH:6]=[CH:5][C:4]=2[C:3]([NH2:21])=[C:2]([CH3:1])[CH:10]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 867016685-Methyl-1-tosyl-1H-indol-4-amine

Product 1

HCID 867016697-Chloro-5-methyl-1-tosyl-1H-indol-4-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 5-methyl-1-tosyl-1H-indol-4-amine (0.52 g, 1.731 mmol) in acetonitrile (17.31 mL) was added NCS (0.231 g, 1.731 mmol), and the mixture was stirred at 50° C. After 2 hours the reaction was cooled to room temperature, quenched with sat. aq. NaHCO3, and with sat. sodium thiosulfate. The layers were separated and the aqueous layer extracted with EtOAc (twice), dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-80% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 335.0 (M+H).

Workup

  1. temperatureAfter 2 hours the reaction was cooled to room temperature
  2. customquenched with sat. aq. NaHCO3
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (twice),
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe resulting residue was purified by flash chromatography (0-80% EtOAc in heptanes)

Sources & evidence

ORD record
ord-caf30f4973174cb2bc36c2116002159a
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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