Pyridine → 1-Phenyl-1H-pyrrolo[3,2-b]pyridine

HRID 347905

Reaktionsgleichung

Reaktionsgleichung von HRID 347905
[NH:1]1[C:9]2[C:4](=[N:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10]1(B(O)O)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(N(CC)CC)C.N1C=CC=CC=1>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:10]1([N:1]2[C:9]3[C:4](=[N:5][CH:6]=[CH:7][CH:8]=3)[CH:3]=[CH:2]2)[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Komponenten

7

Edukt 4

HCID 1049PyridineHCID 8471TriethylamineHCID 92264-AzaindoleHCID 66827Phenylboronic Acid

Produkt 1

HCID 210839631-Phenyl-1H-pyrrolo[3,2-b]pyridineAusbeute 39,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

1H-Pyrrolo[3,2-b]pyridine (0.5 g, 4.24 mmol), phenylboronic acid (1.03 g, 8.44 mmol), copper(II) acetate (1.54 g, 8.48 mmol), and 4A molecular sieves (2 g), were suspended in DCM (10 mL). Triethylamine (1.19 mL, 8.5 mmol) and pyridine (0.7 mL, 8.65 mmol) were added and the reaction stirred at r.t. for three days. The reaction mixture was diluted with further DCM, filtered and concentrated in vacuo. Chromatography (silica, EtOAc) gave the title compound (325 mg). δH (CDCl3) 7.80 (1H, d, J 8.2 Hz), 7.54–7.30 (7H, m), 7.15 (1H, brs), 6.88 (1H, brs). LCMS (ES+) RT 1.20 minutes, 195 (M+H)+.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-2f4441f43afe4a7a8bcb4cfbf57ac8f6
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07176215B2

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