Pyridine → HCID 46912083, Verbindung

HRID 1678141Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1678141
[Cl:1][C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH:11]=[O:12].[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.N1C=CC=CC=1>ClCCl>[Cl:1][C:2]1[N:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]=1[CH:11]=[O:12]

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 469417132-Chloro-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde

Produkt 1

HCID 46912083HCID 46912083, VerbindungAusbeute 25 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 2-chloro-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (70 mg, 0.39 mmol) cupric acetate (140 mg, 0.77 mmol), phenylboronic acid (93 mg, 0.76 mmol), 4A molecular sieve (200 mg), triethylamine (106 μl), pyridine (61 μL) and dichloromethane (5.5 mL) is vigorously stirred at room temperature for 48 hr. The solids are removed by filtration through a pad of Hi-Flo and the filtrate is concentrated. The residue is purified by chromatography eluting with dichloromethane-2% methanol. Product containing fractions are combined and concentrated to give 2-chloro-1-phenyl-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde (25 mg, 25% yield) as a pale yellow oil.

Aufarbeitung

  1. customThe solids are removed by filtration through a pad of Hi-Flo
  2. concentrationthe filtrate is concentrated
  3. customThe residue is purified by chromatography
  4. washeluting with dichloromethane-2% methanol
  5. additionProduct containing fractions
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-e237e1a52e334dfebd799ae6ccdfb027
Quelldatensatz
uspto-grants-2011_08
Patentnummer
US08008491B2

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