3-Bromo-5-methylpyridine → tert-Butyl N-methyl-N-[2-[methyl-(5-methyl-3-pyridyl)amino]ethyl]carbamate

HRID 631823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 631823
Br[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1.[CH3:9][N:10]([CH2:18][CH2:19][NH:20][CH3:21])[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14].CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:9][N:10]([CH2:18][CH2:19][N:20]([CH3:21])[C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH3:8])[CH:7]=1)[C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14]

Komponenten

7

Edukt 4

HCID 8177133-Bromo-5-methylpyridineHCID 14403871tert-Butyl methyl(2-(methylamino)ethyl)carbamateHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenylHCID 23676156Sodium t-butoxide

Produkt 1

HCID 131735429tert-Butyl N-methyl-N-[2-[methyl-(5-methyl-3-pyridyl)amino]ethyl]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

3-Bromo-5-methylpyridine (350 mg, 2.035 mmol), tert-butyl N-methyl-N-(2-methylaminoethyl)carbamate (686 mg, 3.05 mmol), RuPhos (47.5 mg, 0.102 mmol) and sodium tert-butoxide (489 mg, 5.09 mmol) were combined in anhydrous toluene (15 ml). The mixture was purged with argon, tris(dibenzylideneacetone)dipalladium (0) chloroform complex (105 mg, 0.102 mmol) was added and the mixture was stirred at 100° C. overnight. The mixture was filtered through kieselguhr, concentrated under reduced pressure and the residue was purified by column chromatography (silica, gradient of 10 to 50% ethyl acetate in heptane) to yield 301 mg (1.078 mmol, 53%) MS(ESI) m/z=280.2 [M+1]+.

Aufarbeitung

  1. additionwas added
  2. filtrationThe mixture was filtered through kieselguhr
  3. concentrationconcentrated under reduced pressure
  4. customthe residue was purified by column chromatography (silica, gradient of 10 to 50% ethyl acetate in heptane)
  5. customto yield 301 mg (1.078 mmol, 53%) MS(ESI) m/z=280.2 [M+1]+

Quellen und Nachweise

ORD-Eintrag
ord-77721046e93a43d5a6d4bd21ad4f321d
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321724B2

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