Pyridine → 1-(4-tert-butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde

HRID 751368Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 751368
[Cl:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:13]([C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14].N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:13]([C:17]1[CH:22]=[CH:21][C:20]([N:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[C:10]([CH:11]=[O:12])=[C:2]2[Cl:1])=[CH:19][CH:18]=1)([CH3:16])([CH3:15])[CH3:14]

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 3147912-chloro-1H-indole-3-carbaldehydeHCID 27343204-tert-Butylphenylboronic acid

Produkt 1

HCID 860359201-(4-tert-butylphenyl)-2-chloro-1H-indole-3-carboxaldehydeAusbeute 81 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

A mixture of 2-chloro-1H-indole-3-carboxaldehyde (2.2 g, 12.25 mmol), 4-t-butylphenylboronic acid (4.36 g, 24.49 mmol), copper acetate (4.45 g, 24.50 mmol), 4A molecular sieve (2.5 g), pyridine (3.0 mL) and dichloromethane (40 mL) is stirred overnight at room temperature. The reaction mixture is diluted with dichloromethane (100 mL), washed with water (50 mL), with 3N aqueous hydrochloric acid (10 mL), the precipitate removed by filtration and the dichloromethane layer is washed again with water (50 mL), aq sodium bicarbonate, with brine, dried and filtered. The filtrate is concentrated to give a solid. The crude is crystallized from dichloromethane-methanol to afford 1-(4-tert-butylphenyl)-2-chloro-1H-indole-3-carboxaldehyde (3.09 g, 81% yield) as a yellow solid. TLC (silica gel, 20% ethyl acetate/heptane) Rf 0.50; ESI/MS 312 (M+H), RT 4.32 min; NMR: 10.12 (1H, s); 8.20 (1H, d, J=6 Hz); 7.71 (2H, d); 7.53 (2H, d); 7.38 (2H, m); 7.11 (1H, d); 1.38 (9H, s).

Aufarbeitung

  1. washwashed with water (50 mL), with 3N aqueous hydrochloric acid (10 mL)
  2. customthe precipitate removed by filtration
  3. washthe dichloromethane layer is washed again with water (50 mL), aq sodium bicarbonate, with brine
  4. customdried
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated
  7. customto give a solid
  8. customThe crude is crystallized from dichloromethane-methanol

Quellen und Nachweise

ORD-Eintrag
ord-0410b48cd3a949ae8c3ecba5c924e05e
Quelldatensatz
uspto-grants-2008_07
Patentnummer
US07405300B2

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