4-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene → HCID 22287717, compound

HRID 1683919Notes

Reaction equation

HRID 1683919 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17].Cl[C:19]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:20]=1[N+:29]([O-:31])=[O:30].C(N(CC)CC)C>C(O)C>[CH3:17][N:13]1[CH2:14][CH2:15][CH2:16][CH:12]1[CH2:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][C:19]3[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:26])[F:27])=[CH:21][C:20]=3[N+:29]([O-:31])=[O:30])[CH:3]=2)[NH:7][CH:6]=1

Participants

5

Reactant 3

HCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 8471TriethylamineHCID 10376533(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Product 1

HCID 22287717HCID 22287717, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole and 4-chloro-3-nitrobenzotrifluoride were used. Triethylamine was used as base, absolute ethanol was used as solvent, and the reaction was heated at reflux for 4.5 hours. Column chromatography afforded the title compound (38%) as a red foam: Rf =0.30 in 9:1:0.1 [methylene chloride/methanol/ammonium hydroxide]; 13C NMR (CDCl3) δ147.0, 139.7, 135.1, 131.6, 131.0, 129.2, 128.5, 124.7, 124.2, 120.7, 118.6, 116.8, 116.6, 113.6, 112.6, 67.1, 57.4, 40.8, 31.3, 29.2, 21.9. FAB LRMS 419 [MH+]. Anal. calcd for C21H21N4O2.0.6 CH2Cl2 : C, 55.27; H, 4.77; N, 11.94. Found: C, 55.44; H 4.58; N 11.52.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 4.5 hours

Sources & evidence

ORD record
ord-5969af81e270401184f7c11e35c5b4d3
Source dataset
uspto-grants-1997_06
Patent number
US05639752

Reaction notes

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