(2-Methylpropyl)boronic acid → 8-Isobutyl-2,4-dimethyl-5,6-dihydrobenzo[c]acridine

HRID 716592

Reaktionsgleichung

Reaktionsgleichung von HRID 716592
Cl[C:2]1[C:15]2[C:6](=[N:7][C:8]3[C:9]4[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:10]=4[CH2:11][CH2:12][C:13]=3[CH:14]=2)[CH:5]=[CH:4][CH:3]=1.[CH2:22](B(O)O)[CH:23]([CH3:25])[CH3:24]>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].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=CC=2OC)CCCCC1>[CH2:22]([C:2]1[C:15]2[C:6](=[N:7][C:8]3[C:9]4[CH:19]=[C:18]([CH3:20])[CH:17]=[C:16]([CH3:21])[C:10]=4[CH2:11][CH2:12][C:13]=3[CH:14]=2)[CH:5]=[CH:4][CH:3]=1)[CH:23]([CH3:25])[CH3:24]

Komponenten

6

Edukt 2

HCID 2734395(2-Methylpropyl)boronic acidHCID 712451148-Chloro-2,4-dimethyl-5,6-dihydrobenzo[c]acridine

Produkt 1

HCID 712450678-Isobutyl-2,4-dimethyl-5,6-dihydrobenzo[c]acridineAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

8-chloro-2,4-dimethyl-5,6-dihydrobenzo[c]acridine (15.0 g, 51.1 mmol), isobutylboronic acid (7.8 g, 77 mmol), dicyclohexyl(2′,6′-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine (1.6 g, 4.08 mmol) potassium phosphate monohydrate (41.2 g, 179 mmol) were mixed in 300 mL of toluene. The system was degassed for 20 minutes. Pd2(dba)3 (0.93 g, 1.02 mmol) was then added and the system was refluxed overnight. After cooling to room temperature, the reaction mixture was filtered through a Celite® plug and eluted with 30% ethyl acetate in toluene. ˜19.5 crude liquid was obtained. The crude product was recrystallized from 5% acetone in hexane to obtain ˜14.9 g pure product (99.6%) which was confirmed by GC-MS.

Aufarbeitung

  1. customThe system was degassed for 20 minutes
  2. temperaturethe system was refluxed overnight
  3. filtrationthe reaction mixture was filtered through a Celite® plug
  4. washeluted with 30% ethyl acetate in toluene
  5. custom˜19.5 crude liquid was obtained
  6. customThe crude product was recrystallized from 5% acetone in hexane

Quellen und Nachweise

ORD-Eintrag
ord-0a2f15c120b34d139e1f4897172644b0
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09190621B2

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