Potassium Phosphate, Tribasic → 2-(2-(4-methoxybenzylamino)-3-(tetrahydro-2H-pyran-4-yl) quinolin-6-yl)-3-methylbenzonitrile

HRID 1029015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1029015
Br[C:2]1[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH3:11][O:12][C:13]1[CH:45]=[CH:44][C:16]([CH2:17][NH:18][C:19]2[C:28]([CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24](B4OC(C)(C)C(C)(C)O4)[CH:25]=3)[N:20]=2)=[CH:15][CH:14]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(CCC)=CC(CCC)=CC=2CCC)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>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]>[CH3:11][O:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:17][NH:18][C:19]2[C:28]([CH:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[C:24]([C:2]4[C:9]([CH3:10])=[CH:8][CH:7]=[CH:6][C:3]=4[C:4]#[N:5])[CH:25]=3)[N:20]=2)=[CH:44][CH:45]=1

Komponenten

6

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 154691152-Bromo-3-methylbenzonitrileHCID 21081571Dicyclohexyl(2',4',6'-tripropyl-[1,1'-biphenyl]-2-yl)phosphineHCID 71253356N-(4-methoxybenzyl)-3-(tetrahydro-2H-pyran-4-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine

Produkt 1

HCID 673256072-(2-(4-methoxybenzylamino)-3-(tetrahydro-2H-pyran-4-yl) quinolin-6-yl)-3-methylbenzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 2-bromo-3-methylbenzonitrile (0.744 g, 3.79 mmol), N-(4-methoxybenzyl)-3-(tetrahydro-2H-pyran-4-yl)-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)quinolin-2-amine (0.60 g, 1.265 mmol), 2-(dicyclohexylphosphino)-2′,4′,6′,-tri-1-propyl-1,1′-biphenyl (0.121 g, 0.253 mmol), potassium phosphate, anhydrous (0.524 mL, 6.32 mmol), and Pd2(dba)3 (0.116 g, 0.126 mmol) was purged with N2 followed by the addition of degassed dioxane (2 mL) and degassed water (1.0 mL). The resulting mixture was heated in microwave at 140° C. for 12 min. The reaction went to completion and it was filtered, concentrated, and chromatographed on silica gel using gradient 2:1 hexanes/EtOAc to afford a yellow solid as (2-(2-(4-methoxybenzylamino)-3-(tetrahydro-2H-pyran-4-yl) quinolin-6-yl)-3-methylbenzonitrile.

Aufarbeitung

  1. customwas purged with N2
  2. additionfollowed by the addition of degassed dioxane (2 mL)
  3. customdegassed water (1.0 mL)
  4. filtrationwas filtered
  5. concentrationconcentrated
  6. customchromatographed on silica gel using gradient 2:1 hexanes/EtOAc

Quellen und Nachweise

ORD-Eintrag
ord-39d46e396bbf4533a4f470ac98ea578f
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735384B2

Notizen zur Reaktion

Wird geladen…