1,2-Dichloroethane → N-methyl-1H-indole-2-carboxamide

HRID 1362430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1362430
C(Cl)CCl.[NH:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[C:6]1[C:14]([OH:16])=O.CN.C(O)C.C1C=CC2N(O)N=[N:28][C:26]=2C=1.CCN(C(C)C)C(C)C>C1COCC1>[CH3:26][NH:28][C:14]([C:6]1[NH:5][C:13]2[C:8]([CH:7]=1)=[CH:9][CH:10]=[CH:11][CH:12]=2)=[O:16]

Komponenten

8

Edukt 6

HCID 111,2-DichloroethaneHCID 702EthanolHCID 6329MethylamineHCID 72899Indole-2-carboxylic acidHCID 757711-HydroxybenzotriazoleHCID 81531Diisopropylethylamine

Produkt 1

HCID 12461785N-methyl-1H-indole-2-carboxamideAusbeute 153,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

EDC (7.7 g, 40.3 mmol) was added to a solution of indole-2-carboxylic acid (5 g, 13.1 mmol), methylamine, 33% in ethanol (5.6 mL, 15.5 mmol), HOBT (4.1 g, 13.1 mmol) and DIPEA (2.1 mL, 12.4 mmol) in THF, anhydrous (45 mL) and stirred overnight. The crude mixture was evaporated in vacuo and chromatographed over silica eluting with methanol/dichloromethane (0-2%) to afford the title compound (3.51 g, 66%). 1H NMR (300 MHz, DMSO-d6) δ 11.53 (s, 1H), 8.43 (s, 1H), 7.57 (d, J=7.9 Hz, 1H), 7.39 (d, J=8.2 Hz, 1H), 7.15 (t, J=8.2 Hz, 1H), 7.03 (s, 1H), 6.98 (t, J=7.9 Hz, 1H), 2.79 (d, J=4.7 Hz, 3H)

Aufarbeitung

  1. customThe crude mixture was evaporated in vacuo
  2. customchromatographed over silica eluting with methanol/dichloromethane (0-2%)

Quellen und Nachweise

ORD-Eintrag
ord-ec51eab26da8492aa2c1e886d434cd7b
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07879872B2

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