Pyridine → HCID 86621676, Verbindung

HRID 1364117Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1364117
[N:1]1[NH:2][CH:3]=[C:4]2[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6][C:5]=12.[Br:18][C:19]1[N:24]=[CH:23][C:22](B(O)O)=[CH:21][CH:20]=1.N1C=CC=CC=1>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Br:18][C:19]1[N:24]=[CH:23][C:22]([N:2]2[CH:3]=[C:4]3[C:5]([CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10]3)=[N:1]2)=[CH:21][CH:20]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 27627062-Bromopyridine-5-boronic acidHCID 178451637HCID 178451637, Verbindung

Produkt 1

HCID 86621676HCID 86621676, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8895Cupric acetateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1,1-dimethylethyl 4,5,7,8-tetrahydropyrazolo[3,4-d]azepine-6(2H)-carboxylate (may be prepared as described in Description 9) (207 mg, 0.87 mmol), (6-bromo-3-pyridinyl)boronic acid (204 mg, 1.74 mmol), copper acetate (472 mg, 2.61 mmol), pyridine (140 μl, 1.74 mmol) and molecular sieves (4 Å, 750 mg) in dichloromethane (10 ml) was stirred open to the atmosphere for 8 days. Crude mixture was then filtered through a pad of celite and washed with dichloromethane and ammonia. After evaporation in vacuo, the residue was purified by SCX cartridge eluting with methanol first then 2M ammonia in methanol. The methanol fractions containing the product were combined and evaporated in vacuo. The residue was then purified by column chromatography on silica gel eluting with a mixture of hexane in ethyl acetate (10:1 to 1:1) to afford the title compound (D17). MS (ES+) m/e 393 and 395 [M+H]+.

Aufarbeitung

  1. filtrationCrude mixture was then filtered through a pad of celite
  2. washwashed with dichloromethane and ammonia
  3. customAfter evaporation in vacuo
  4. customthe residue was purified by SCX cartridge
  5. washeluting with methanol first
  6. additionThe methanol fractions containing the product
  7. customevaporated in vacuo
  8. customThe residue was then purified by column chromatography on silica gel eluting with a mixture of hexane in ethyl acetate (10:1 to 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-7f029a5836eb492894b9407909383a87
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07888347B2

Notizen zur Reaktion

Wird geladen…