Trifluoroacetic acid → 2-(2-chloro-6-methoxy-phenyl)-1H-indol-6-ylamine

HRID 1051228Notes

Reaction equation

HRID 1051228 reaction equation
C(OC(=O)[NH:7][C:8]1[CH:16]=[C:15]2[C:11]([CH:12]=[C:13]([C:17]3[C:22]([O:23][CH3:24])=[CH:21][CH:20]=[CH:19][C:18]=3[Cl:25])[NH:14]2)=[CH:10][CH:9]=1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:25][C:18]1[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH3:24])[C:17]=1[C:13]1[NH:14][C:15]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[C:8]([NH2:7])[CH:16]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 90102905[2-(2-chloro-6-methoxy-phenyl)-1H-indol-6-yl]-carbamic acid tert-butyl ester

Product 1

HCID 742207322-(2-chloro-6-methoxy-phenyl)-1H-indol-6-ylamineYield 91.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of [2-(2-chloro-6-methoxy-phenyl)-1H-indol-6-yl]-carbamic acid tert-butyl ester (120 mg, 0.32 mmol) in CH2Cl2 (5 mL) was added 2,2,2-trifluoroacetic acid (0.5 mL) at 25° C. The solution was heated to reflux for 3 h, concentrated and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (70/30 hexanes/ethyl acetate) afforded 2-(2-chloro-6-methoxy-phenyl)-1H-indol-6-ylamine (80 mg, 91%) as a white solid. MH+ 272.9.

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for 3 h
  3. concentrationconcentrated
  4. additionpoured into water
  5. extractionThe aqueous phase was extracted three times with ethyl acetate
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationFiltration
  9. concentrationfollowed by concentration in vacuo
  10. customgave a brown solid

Sources & evidence

ORD record
ord-31d88b4deee84ff89e3ea5126849925c
Source dataset
uspto-grants-2016_07
Patent number
US09388166B2

Reaction notes

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