Trifluoroacetic acid → (E)-2-amino-1-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)ethanone

HRID 1502706Notes

Reaction equation

HRID 1502706 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]([C:33]([F:36])([F:35])[F:34])/[CH:11]=[CH:12]/[C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:22](=[O:32])[CH2:23][NH:24]C(=O)OC(C)(C)C)[CH:17]=[CH:16]3)[CH:5]=[C:6]([Cl:9])[C:7]=1[F:8].C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:24][CH2:23][C:22]([N:18]1[C:19]2[C:15](=[CH:14][C:13](/[CH:12]=[CH:11]/[CH:10]([C:4]3[CH:3]=[C:2]([Cl:1])[C:7]([F:8])=[C:6]([Cl:9])[CH:5]=3)[C:33]([F:35])([F:36])[F:34])=[CH:21][CH:20]=2)[CH:16]=[CH:17]1)=[O:32]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86675171(E)-tert-butyl 2-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)-2-oxoethylcarbamate

Product 1

HCID 86675170(E)-2-amino-1-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of (E)-tert-butyl 2-(5-(3-(3,5-dichloro-4-fluorophenyl)-4,4,4-trifluorobut-1-enyl)-1H-indol-1-yl)-2-oxoethylcarbamate (0.05 g, 0.09 mmol) in CH2Cl2 (5.0 mL) was added TFA (0.01 mL) and the reaction was stirred at ambient temperature for 16 h. The reaction mixture was diluted with CH2Cl2 and washed with saturated NaHCO3 solution, water and brine solution. The separated CH2Cl2 layer was dried over anhydrous Na2SO4 and concentrated under reduced pressure to afford the crude title compound which was used in the next step without further purification (50 mg).

Workup

  1. washwashed with saturated NaHCO3 solution, water and brine solution
  2. dry with materialThe separated CH2Cl2 layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fa8f59d4a77c422d93ce9f54244a4d03
Source dataset
uspto-grants-2015_12
Patent number
US09210927B2

Reaction notes

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