Trifluoroacetic acid → 2-[3-(2-Aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-azabicyclo[2.2.1]hept-7-yl)-2-methyl-propan-1-one

HRID 612748Notes

Reaction equation

HRID 612748 reaction equation
C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O.C(OC(=O)[NH:22][CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:34]([CH3:45])([CH3:44])[C:35]([N:37]3[CH:41]4[CH2:42][CH2:43][CH:38]3[CH2:39][CH2:40]4)=[O:36])[CH:32]=2)[NH:27][C:26]=1[C:46]1[CH:51]=[C:50]([CH3:52])[CH:49]=[C:48]([CH3:53])[CH:47]=1)(C)(C)C>>[NH2:22][CH2:23][CH2:24][C:25]1[C:33]2[C:28](=[CH:29][CH:30]=[C:31]([C:34]([CH3:45])([CH3:44])[C:35]([N:37]3[CH:38]4[CH2:39][CH2:40][CH:41]3[CH2:42][CH2:43]4)=[O:36])[CH:32]=2)[NH:27][C:26]=1[C:46]1[CH:51]=[C:50]([CH3:52])[CH:49]=[C:48]([CH3:53])[CH:47]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 11114148{2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}carbamic acid tert-butyl ester

Product 1

HCID 117617912-[3-(2-Aminoethyl)-2-(3,5-dimethylphenyl)-1H-indol-5-yl]-1-(7-azabicyclo[2.2.1]hept-7-yl)-2-methyl-propan-1-oneYield 106.2%

Conditions

Temperature
0 °C

Procedure

To a solution of {2-[5-[2-(7-azabicyclo[2.2.1]hept-7-yl)-1,1-dimethyl-2-oxo-ethyl]-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl} carbamic acid tert-butyl ester (728 mg in 30 mL methylene chloride) at 0° C. was added 1.5 mL anisole followed by 10.5 mL trifluoroacetic acid and the mixture stirred at 0° C. After 2 hours, the mixture was concentrated in vacuo and the residual acid quenched by the addition of 10% ammonium hydroxide in methanol. The concentrated was then purified by flash chromatography on silica gel (methylene chloride:10% ammonium hydroxide in methanol, 95:5; then 92:8) to give the title compound (627 mg).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customthe residual acid quenched by the addition of 10% ammonium hydroxide in methanol
  3. customThe concentrated was then purified by flash chromatography on silica gel (methylene chloride

Sources & evidence

ORD record
ord-55969166d8934bd6a51e2947a82c70c0
Source dataset
uspto-grants-1999_12
Patent number
US06004984

Reaction notes

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