Indole → N-methoxy-N-methyl-3-(indol-5-yl)acrylamide

HRID 2416251

Reaktionsgleichung

Reaktionsgleichung von HRID 2416251
[H-].[Na+].C(OP([CH2:11][C:12](=[O:17])[N:13]([O:15][CH3:16])[CH3:14])(=O)OCC)C.[NH:18]1[C:26]2[C:21](=[CH:22][C:23]([CH:27]=O)=[CH:24][CH:25]=2)[CH:20]=[CH:19]1.N1C2C(=CC=CC=2)C=C1>C1COCC1>[CH3:16][O:15][N:13]([CH3:14])[C:12](=[O:17])[CH:11]=[CH:27][C:23]1[CH:22]=[C:21]2[C:26](=[CH:25][CH:24]=1)[NH:18][CH:19]=[CH:20]2

Komponenten

6

Edukt 4

HCID 798IndoleHCID 24758Sodium hydrideHCID 589040Indole-5-carboxaldehydeHCID 2773719Diethyl (N-methoxy-N-methylcarbamoylmethyl)phosphonate

Produkt 1

HCID 73990728N-methoxy-N-methyl-3-(indol-5-yl)acrylamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of sodium hydride (0.44 g of a 60% suspension in mineral oil, 11 mmol) and diethyl-(N-methoxy-N-methyl-carbamoylmethyl)-phosphonate (3.0 g, 3 equiv.) in anhydrous THF was stirred at room temperature for 30 minutes. A solution of indole-5-carboxaldehyde (0.61 g, 4.18 mmol) was added dropwise to the mixture. The reaction was complete after 2 h after the addition of the starting indole. The mixture was quenched with water (50 ml), then diluted with ether. The organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give N-methoxy-N-methyl-3-(indol-5-yl)acrylamide as a yellow oil which solidified on standing to an off-white solid (1.53 g, quantitative yield. 1H NMR (CDCl3): δ 8.55 (br, 1H), 7.87 (d, J=18.6 Hz, 1H), 7.85 (s, 1H), 7.38 (d, J=8.5 Hz, 1H), 7.25 (d, J=8.5 Hz, 1H), 7.23 (m, 1H), 7.0 (d, J=18.6 Hz, 1H), 6.58 (m, 1H), 3.78 (s, 3H), and 3.32 (s, 3H). FIMS: 229.1 (M−H)−, reverse-phase HPLC purity: 88%.

Aufarbeitung

  1. waitThe reaction was complete after 2 h
  2. customThe mixture was quenched with water (50 ml)
  3. additiondiluted with ether
  4. customThe organic layer was separated
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-f44874bf1e5b4fa0b34df2f9247b398e
Quelldatensatz
uspto-grants-2004_11
Patentnummer
US06822100B2

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