Sodium Carbonate → 1-(6-Bromopyridin-2-yl)-N-[(3-isopropyl-1,2,4-oxadiazol-5-yl)methyl]methanamine

HRID 385772Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385772
[Br:1][C:2]1[N:7]=[C:6]([CH:8]=O)[CH:5]=[CH:4][CH:3]=1.[CH:10]([C:13]1[N:17]=[C:16]([CH2:18][NH2:19])[O:15][N:14]=1)([CH3:12])[CH3:11].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>ClC(Cl)C.C(OCC)(=O)C>[Br:1][C:2]1[N:7]=[C:6]([CH2:8][NH:19][CH2:18][C:16]2[O:15][N:14]=[C:13]([CH:10]([CH3:12])[CH3:11])[N:17]=2)[CH:5]=[CH:4][CH:3]=1

Komponenten

8

Edukt 5

HCID 10340Sodium CarbonateHCID 516892Sodium BicarbonateHCID 27570096-Bromopyridine-2-carbaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 280631563-(1-Methylethyl)-1,2,4-oxadiazole-5-methanamine

Produkt 1

HCID 595257901-(6-Bromopyridin-2-yl)-N-[(3-isopropyl-1,2,4-oxadiazol-5-yl)methyl]methanamine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 63651,1-DichloroethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6-Bromopyridine-2-carbaldehyde (1.18 g, 6.34 mmol) and 1-(3-isopropyl-1,2,4-oxadiazol-5-yl)methanamine (0.90 g, 6.34 mmol) were combined and dissolved in dichloroethane (26.0 ml), reacted for 45 minutes, at which time sodium triacetoxyborohydride (1.88 g, 8.88 mmol) was added and the reaction was maintained at room temperature overnight. The reaction was diluted with ethyl acetate followed by the addition of saturated sodium bicarbonate and saturated sodium carbonate to make sure the pH was basic. The organic layer was separated and washed with brine. The organic layer was dried over magnesium sulfate, filtered and concentrated. The crude reaction mixture was purified by silica gel chromatography to yield the title compound.

Aufarbeitung

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude reaction mixture
  8. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-f4f9b17f558c4953bed704779e9f12d9
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367706B2

Notizen zur Reaktion

Wird geladen…