Phenylsilane → Methyl 4-([2,3']bipyridinyl-6-ylaminomethyl)-benzoate

HRID 852902Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 852902
[N:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[CH:3][C:2]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[CH:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=O.C1([SiH3])C=CC=CC=1>C1COCC1.C([Sn](Cl)(Cl)CCCC)CCC>[N:1]1[C:6]([NH:7][CH2:14][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)=[CH:5][CH:4]=[CH:3][C:2]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1

Komponenten

6

Edukt 3

HCID 12752PhenylsilaneHCID 15294Methyl 4-FormylbenzoateHCID 11586359[2,3'-Bipyridin]-6-amine

Produkt 1

HCID 58930610Methyl 4-([2,3']bipyridinyl-6-ylaminomethyl)-benzoateAusbeute 98,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 12688Dibutyltin dichlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirred suspension of a mixture of 11 (3.00 g, 17.52 mmol), methyl 4-formylbenzoate (4.62 g, 28.11 mmol, 1.5-2.0 equiv.) and dibutyl tin dichloride 160 mg, 0.53 mmol) in anhydrous THF (15 mL) at room temperature was added phenylsilane (2.34 mL, 19.28 mmol) in three portions over two days. After stirring for 2 to 7 days the reaction mixture was filtered, filtrate was concentrated and purified by flash chromatography on silica gel (MeOH/CH2Cl2, 2/98→10/90) to afford the title compound 12 (5.50 g, 17.22 mmol, 98% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.11 (dd, J=2.3, 0.7 Hz, 1H), 8.55 (dd, J=4.7, 1.8 Hz, 1H), 8.29-8.24 (m, 1H), 7.93 (d, J=8.4 Hz, 2H), 7.57-7.40 (m, 5H), 7.18 (d, J=7.2 Hz, 1H), 6.59 (d, J=8.2 Hz 1H), 4.69 (d, J=6.1 Hz, 2H), 3.85 (s, 3H).

Aufarbeitung

  1. filtrationwas filtered
  2. concentrationfiltrate was concentrated
  3. custompurified by flash chromatography on silica gel (MeOH/CH2Cl2, 2/98→10/90)

Quellen und Nachweise

ORD-Eintrag
ord-cdbb4155d2954433adc05ef0eed4ec93
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07253204B2

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