Trifluoroacetic acid → 5-Methyl-1-tosyl-1H-indol-4-amine

HRID 2174045Notes

Reaction equation

HRID 2174045 reaction equation
[CH3:1][C:2]1[C:3]([NH:21]C(=O)OC(C)(C)C)=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([S:11]([C:14]1[CH:20]=[CH:19][C:17]([CH3:18])=[CH:16][CH:15]=1)(=[O:13])=[O:12])[CH:6]=[CH:5]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[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]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86701666tert-Butyl (5-methyl-1-tosyl-1H-indol-4-yl)carbamate

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl (5-methyl-1-tosyl-1H-indol-4-yl)carbamate (10.5 g, 26.2 mmol) in DCM (197 mL) was added TFA (65.5 mL), and the mixture was stirred at room temperature. After 20 minutes the reaction was concentrated, dissolved in EtOAc, washed with sat. aq. NaHCO3, dried over MgSO4, filtered and concentrated. The resulting residue was purified by flash chromatography (0-70% EtOAc in heptanes) to provide the title compound. MS (ESI+) m/z 301.1 (M+H).

Workup

  1. concentrationAfter 20 minutes the reaction was concentrated
  2. dissolutiondissolved in EtOAc
  3. washwashed with sat. aq. NaHCO3
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe resulting residue was purified by flash chromatography (0-70% EtOAc in heptanes)

Sources & evidence

ORD record
ord-d1969f0c74b444ce9fe0f24b4e33138b
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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