Triethylamine → HCID 54360035, Verbindung

HRID 1683914Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1683914
[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[C:24]([N+:25]([O-:27])=[O:26])=[C:23]([CH3:28])[CH:22]=[CH:21][N:20]=1.C(N(CC)CC)C>C(O)C>[CH3:28][C:23]1[CH:22]=[CH:21][N:20]=[C:19]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH2:11][CH:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH3:17])[C:24]=1[N+:25]([O-:27])=[O:26]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 3453632-Chloro-4-methyl-3-nitropyridineHCID 10376533(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

Produkt 1

HCID 54360035HCID 54360035, VerbindungAusbeute 34 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

(R)-5-Amino-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole and 2-chloro-4-methyl-3-nitropyridine were used. Triethylamine was used as base, absolute ethanol was used as solvent, and the reaction was heated at reflux for 24 hours. Column chromatography afforded the title compound (34%) as a red amorphous solid: 1H NMR (CDCl3) δ9.26 (brs, NH),8.79 (brs, NH),8.10 (d,J=4.8 Hz, 1H), 7.64(d,J=1.7 Hz, 1H), 7.29 (d, J=8.5 Hz, 1H), 7.17 (dd, J=8.5 and 1.9 Hz, 1H), 6.97 (d, J=2.2 Hz, 1H), 6.56 (d, J=4.8 Hz, 1H), 3.25-3.16 (m, 2H), 2.67 (dd, J=13.2 and 9.4 Hz, 1H), 2.64-2.56 (m, 1H), 2.56 (s, 3H), 2.46 (s, 3H), 2.30 (dd, J=17.7 and 9.4 Hz, 1H), 1.90-1.60 (m, 4H); 13C NMR (CDCl3) δ152.2, 151.5, 146.6, 134.3, 131.0, 130.0, 127.9, 123.4, 119.4, 117.1, 114.0, 113.3, 111.6, 67.0, 57.4, 40.7, 31.4, 29.5, 21.8, 21.7; FAB HRMS calculated for [C20H23N5O2.H]366.1932, found 366.1957.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-bef87abd07a14b38a4ce3490c8ca64ac
Quelldatensatz
uspto-grants-1997_06
Patentnummer
US05639752

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