Ethyl Acetate → 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylic acid (4-tert-butylphenyl)-amide

HRID 1514932

Reaktionsgleichung

Reaktionsgleichung von HRID 1514932
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[C:9]1[NH:10][C:11]2[C:16]([CH:17]=1)=[CH:15][CH:14]=[C:13]([C:18](O)=[O:19])[CH:12]=2.[C:21]([C:25]1[CH:31]=[CH:30][C:28]([NH2:29])=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(OCC)(=O)C>CN(C=O)C>[C:21]([C:25]1[CH:26]=[CH:27][C:28]([NH:29][C:18]([C:13]2[CH:12]=[C:11]3[C:16]([CH:17]=[C:9]([C:3]4[C:4]([CH3:8])=[CH:5][CH:6]=[CH:7][C:2]=4[CH3:1])[NH:10]3)=[CH:15][CH:14]=2)=[O:19])=[CH:30][CH:31]=1)([CH3:24])([CH3:22])[CH3:23]

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 698614-Tert-ButylanilineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 669653062-(2,6-dimethylphenyl)-1H-indole-6-carboxylic acid

Produkt 1

HCID 669656932-(2,6-dimethylphenyl)-1H-indole-6-carboxylic acid (4-tert-butylphenyl)-amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylic acid. (17 mg, 60 μmol), 4-tert.-butylaniline (10 μL, 9.4 mg, 63 μmol) and HATU (33 mg, 87 μmol) in DMF (3 mL) was stirred, initially at ambient temperature, then at 60° C. for 18 h. The mixture was poured into ethyl acetate and extracted once with water and five times with brine. The organic layer was dried, filtered, and solvent was removed under reduced pressure. The residual material was chromatographed using a gradient of 20-60% heptane/ethyl acetate to give 2-(2,6-dimethylphenyl)-1H-indole-6-carboxylic acid (4-tert-butylphenyl)-amide. 1H NMR (CDCl3, 400 MHz) δ 8.54 (s, broad, 1H), 8.12 (s, 1H), 7.89 (s, 1H), 7.70 (d, J=8.3 Hz, 1H), 7.56 (m, 3H), 7.37 (d, J=8.7 Hz, 2H), 7.15 (d, J=7.6 Hz, 2H), 6.46 (s, 1H), 2.18 (s, 6H), 1.33 (s, 9H). MS (m/z) 397.2 (M+1).

Aufarbeitung

  1. extractionextracted once with water and five times with brine
  2. customThe organic layer was dried
  3. filtrationfiltered
  4. customsolvent was removed under reduced pressure
  5. customThe residual material was chromatographed

Quellen und Nachweise

ORD-Eintrag
ord-cacfd5e814e447daabc192fc744299d2
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222248B2

Verknüpfte Notizen

Wird geladen…