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Sodium Carbonate → 1-(4-benzylphenyl)-9-(4-hydroxyphenyl)benzo[h][1,6]naphthyridin-2(1H)one

HRID 1944595
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1944595
[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:23]3[C:18](=[CH:19][N:20]=[C:21]4[CH:27]=[CH:26][C:25](Cl)=[CH:24][C:22]4=3)[CH:17]=[CH:16][C:15]2=[O:29])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:30][C:31]1[CH:36]=[CH:35][C:34](B(O)O)=[CH:33][CH:32]=1.C([O-])([O-])=O.[Na+].[Na+].C(P(C(C)(C)C)C1C=CC=CC=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>O1CCOCC1.CCO.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([C:8]1[CH:13]=[CH:12][C:11]([N:14]2[C:23]3[C:18](=[CH:19][N:20]=[C:21]4[CH:27]=[CH:26][C:25]([C:34]5[CH:35]=[CH:36][C:31]([OH:30])=[CH:32][CH:33]=5)=[CH:24][C:22]4=3)[CH:17]=[CH:16][C:15]2=[O:29])=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 10340Sodium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 11618717Di-tert-butyl(2',4',6'-tris(propan-2-yl)-(1,1'-biphenyl)-2-yl)phosphaneHCID 585249781-(4-benzylphenyl)-9-chlorobenzo[h][1,6]naphthyridin-2(1H)-one

Produkt 1

HCID 461916921-(4-benzylphenyl)-9-(4-hydroxyphenyl)benzo[h][1,6]naphthyridin-2(1H)one
Ausbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 1-(4-benzylphenyl)-9-chlorobenzo[h][1,6]naphthyridin-2(1H)-one (100 mg, 0.22 mmol) in 1,4-dioxane (0.6 mL) was added 4-hydroxyphenylboronic acid (45 mg, 0.33 mmol) and 1 N Na2CO3 (0.66 mL, 0.66 mmol). The reaction mixture was degassed using Argon gas for 10 min and added Pd(PPh3)2Cl2 (15 mg, 0.02 mmol) and di-tert-butyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (15 mg, 0.04 mmol). The reaction flask was put into the preheated oil-bath at 100° C. The reaction mixture was further stirred at 100° C. a period of 8 hours after which, it was filtered and partitioned between ethyl acetate and water. The organic layer was separated and the aqueous layer was extracted with ethyl acetate. The combined organic extracts were washed with brine, dried over MgSO4, filtered and concentrated. The crude product was purified by flash column chromatography using a 97:3 v/v CH2Cl2: EtOH as solvent to afford title compound (64 mg, 64% yield) as a yellow solid. 1H NMR 600 MHz (CDCl3) δ 9.08 (s, 1H), 8.42 (s, 1H), 8.04 (d, J=2.4 Hz, 1H), 7.95 (d, J=8.2 Hz, 1H), 7.61 (dd, J=2.1, 6.6 Hz, 1H), 7.25 (m, 2H), 7.12 (m, 4H), 7.00 (m, 5H), 6.75 (d, J=8.4 Hz, 2H), 6.48 (dd, J=2.4, 6.2 Hz, 1H), 3.88 (s, 2H), MS m/z: 455.27 (M+1).

Aufarbeitung

  1. customThe reaction mixture was degassed
  2. customfor 10 min
  3. customwas put into the preheated oil-bath at 100° C
  4. filtrationwas filtered
  5. custompartitioned between ethyl acetate and water
  6. customThe organic layer was separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe combined organic extracts were washed with brine
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated
  12. customThe crude product was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-bc676d62690b4f9385cf7e78f16725e3
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08394818B2

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