Trifluoroacetic acid → Methyl 2-(2-aminophenyl)-3-cyclohexyl-1H-indole-6-carboxylate

HRID 1518220Notes

Reaction equation

HRID 1518220 reaction equation
[C:1](O)(C(F)(F)F)=O.C(OC([NH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[NH:23][C:24]2[C:29]([C:30]=1[CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][CH2:32]1)=[CH:28][CH:27]=[C:26]([C:37]([O-:39])=[O:38])[CH:25]=2)=O)(C)(C)C>C(Cl)Cl>[NH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[NH:23][C:24]2[C:29]([C:30]=1[CH:31]1[CH2:32][CH2:33][CH2:34][CH2:35][CH2:36]1)=[CH:28][CH:27]=[C:26]([C:37]([O:39][CH3:1])=[O:38])[CH:25]=2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 866378522-{[(tert-butoxycarbonyl)amino]phenyl}-3-cyclohexyl-1H-indole-6-carboxylate

Product 1

HCID 11995001Methyl 2-(2-aminophenyl)-3-cyclohexyl-1H-indole-6-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (137 eq) was added to a solution of methyl 2-(2-{[(tert-butoxycarbonyl)amino]phenyl}-3-cyclohexyl-1H-indole-6-carboxylate in DCM (0.1 M) at 0° C. and the solution was allowed to stir at RT for 1 h. The volatiles were removed in vacuo, and the residue diluted with EtOAc. The organic phase was washed with saturated aqueous NaHCO3 (twice) and then brine. The organic phase was dried over Na2SO4, filtered and the solvent evaporated in vacuo to afford the title compound (quant.). MS (ES+) m/z 349 (M+H)+.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe residue diluted with EtOAc
  3. washThe organic phase was washed with saturated aqueous NaHCO3 (twice) and then brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-e17dd9b24da54d648ea1065ff08ba28c
Source dataset
uspto-grants-2012_07
Patent number
US08232390B2

Reaction notes

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