5-Bromonicotinamide → 5-{1'-tert-Butoxycarbonyl-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinamide

HRID 38474

Reaktionsgleichung

Reaktionsgleichung von HRID 38474
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]2([CH2:22][C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18](B4OC(C)(C)C(C)(C)O4)[CH:19]=3)[O:14]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:34]1[CH:35]=[N:36][CH:37]=[C:38]([CH:42]=1)[C:39]([NH2:41])=[O:40].C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C(Cl)(Cl)Cl.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]2([CH2:22][C:21](=[O:23])[C:20]3[C:15](=[CH:16][CH:17]=[C:18]([C:34]4[CH:35]=[N:36][CH:37]=[C:38]([CH:42]=4)[C:39]([NH2:41])=[O:40])[CH:19]=3)[O:14]2)[CH2:12][CH2:13]1)=[O:7])([CH3:2])([CH3:3])[CH3:4]

Komponenten

8

Edukt 3

HCID 18085-BromonicotinamideHCID 10340Sodium CarbonateHCID 579309611'-Tert-butoxycarbonyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[chroman-2,4'-piperidin]-4-one

Produkt 1

HCID 579310025-{1'-tert-Butoxycarbonyl-4-oxospiro[chroman-2,4'-piperidin]-6-yl}nicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6212ChloroformLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

1′-tert-butoxycarbonyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)spiro[chroman-2,4′-piperidin]-4-one (1.43 g, 3.23 mmol), 5-bromonicotinamide (778 mg, 3.87 mmol), Pd(PPh3)4 (372 mg, 0.322 mmol), and aqueous 2M Na2CO3 (10 ml) solution were suspended in dioxane (20 ml) and heated at 100° C. for 4 h. The reaction mixture was diluted with CHCl3 and H2O, the aqueous layer was extracted with CHCl3. The combined organic layer was dried over MgSO4. The desiccant was removed through celite filtration and the filtrate was concentrated under reduced pressure. The resulting residue was purified through silica gel column chromatography (EtOAc/Acetone) to obtain the intended compound as a pale yellow foam.

Aufarbeitung

  1. extractionthe aqueous layer was extracted with CHCl3
  2. dry with materialThe combined organic layer was dried over MgSO4
  3. customThe desiccant was removed through celite filtration
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (EtOAc/Acetone)

Quellen und Nachweise

ORD-Eintrag
ord-7e06f045e1ef42b1b489e3e145c87c11
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524730B2

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