Dibutyltin dichloride → N-[(8-methyl-2-phenylquinolin-3-yl)methyl]quinoxalin-6-amine

HRID 1948743

Reaktionsgleichung

[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([CH:18]=O)=[CH:7]2.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1.[NH2:38][C:39]1[CH:40]=[C:41]2[C:46](=[CH:47][CH:48]=1)[N:45]=[CH:44][CH:43]=[N:42]2>C1COCC1>[CH3:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[N:10]=[C:9]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:8]([CH2:18][NH:38][C:39]1[CH:40]=[C:41]3[C:46](=[CH:47][CH:48]=1)[N:45]=[CH:44][CH:43]=[N:42]3)=[CH:7]2

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

To a solution of 8-methyl-2-phenylquinoline-3-carboxaldehyde (80 mg, 0.32 mmol) in THF (5 mL) was added di-n-butyltin dichloride (10 mg, 0.032 mmol), phenylsilane (70 mg, 0.64 mmol) and 6-aminoquinoxaline (46 mg, 0.32 mmol). The mixture was heated in a microwave at 100° C. for 3 h. Purification by preparative HPLC (Method 2) gave the title compound as an off-white solid (45 mg, 37%). δH (CDCl3) 8.61 (d, J 2.1 Hz, 1H), 8.51 (d, J 1.9 Hz, 1H), 8.24 (s, 1H), 7.84 (d, J 9.0 Hz, 1H), 7.71-7.76 (m, 1H), 7.61-7.66 (m, 1H), 7.40-7.58 (m, 6H), 7.10 (dd, J 9.2, 2.6 Hz, 1H), 6.88 (d, J 2.6 Hz, 1H), 4.64-4.69 (m, 2H), 4.52-4.60 (m, 1H), 2.82 (s, 3H). LCMS (ES+) 377.2 (M+H)+, RT 4.23 minutes (Method 4).

Aufarbeitung

customPurification by preparative HPLC (Method 2)

Quellen und Nachweise

ORD-Eintrag: ord-730f96ec1f05414593bd9d910b5a6018
Quelldatensatz: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08399483B2

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