Triethylamine → HCID 54387087, compound

HRID 1419155Notes

Reaction equation

HRID 1419155 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].C(N(CC)CC)C.[N+:25]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1F)([O-:27])=[O:26]>>[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:29]3[CH:30]=[CH:31][CH:32]=[CH:33][C:28]=3[N+:25]([O-:27])=[O:26])[CH:3]=2)[NH:7][CH:6]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 738951-Fluoro-2-nitrobenzene2×HCID 10376533(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Product 1

HCID 54387087HCID 54387087, compoundYield 48%

Procedure

(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole and o-nitrofluorobenzene were used. Triethylamine was used as base, o-nitrofluorobenzene was used as solvent, and the reaction was heated at reflux for 24 hours. Column chromatography afforded the title compound (48%) as a red amorphous solid: 1H NMR (CDCl3) δ 9.62 (br s, NH), 8.77 (br s, NH), 8.19 (dd, J=8.7 and 1.5 Hz,1H), 7.47 (d, J=1.6 Hz, 1H), 7.38 (d, J=8.5 Hz, 1H), 7.29-7.23 (m, 1H), 7.09-7.00 (m, 3H), 6.69-6.64 (m, 1H), 3.20-3.12 (m, 2H), 2.63 (dd, J=14.0 and 9.5 Hz, 1H), 2.54-2.45 (m, 1H), 2.45 (s, 3H), 2.25 (dd, J=17.1 and 9.2 Hz, 1H), 1.91-1.54 (m, 4H); 13C NMR (CDCl3) δ 145.4, 135.7, 134.8, 132.1, 130.1, 128.6, 126.5, 123.6, 120.7, 116.4, 116.4, 116.1, 114.1, 112.2, 66.7, 57.5, 40.8, 31.5, 29.8, 21.9; FAB HRMS calculated for [C20H22N4O2.H] 351.1823, found 351.1797.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 24 hours

Sources & evidence

ORD record
ord-dd454a14869c4c64b855f079487de6c9
Source dataset
uspto-grants-1999_03
Patent number
US05886008

Reaction notes

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