Methanol → [2-(3-Methyl-4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanone

HRID 609811

Reaktionsgleichung

Reaktionsgleichung von HRID 609811
CN(C)[C:3]1[S:4][C:5]2[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:6]=2[C:7]=1[C:8]([C:10]1[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:12][CH:11]=1)=[O:9].C1COCC1.[CH3:37][C:38]1[CH:39]=[C:40]([Mg]Br)[CH:41]=[CH:42][C:43]=1[O:44][CH3:45].CO>ClC1C=CC=CC=1.C(Cl)Cl>[CH3:37][C:38]1[CH:39]=[C:40]([C:3]2[S:4][C:5]3[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:6]=3[C:7]=2[C:8]([C:10]2[CH:15]=[CH:14][C:13]([O:16][CH2:17][CH2:18][N:19]3[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]3)=[CH:12][CH:11]=2)=[O:9])[CH:41]=[CH:42][C:43]=1[O:44][CH3:45]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 9954835[2-Dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneHCID 178491913HCID 178491913, Verbindung

Produkt 1

HCID 10839573[2-(3-Methyl-4-methoxyphenyl)-6-methoxybenzo[b]thien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]methanoneAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 7964ChlorobenzeneLösungsmittel

Versuchsvorschrift

By the method described in Example 1, [2-dimethylamino-6-methoxybenzothien-3-yl][4-[2-(1-piperidinyl)ethoxy]phenyl]-methanone (1.0 g, 2.3 mmol) in chlorobenzene (10 mL) was treated with a 0.69 M THF solution of 3-methyl-4-methoxyphenylmagnesium bromide (11 mL, 7.6 mmol) (prepared from 4-bromo-2-methylanisole, catalytic iodine, and magnesium turnings in THF) to provide, after chromatography (silica gel, 5-10% MeOH in CH2Cl2) 810 mg (69%) of the title compound as a yellow oil: 1H NMR d 1.43 (m, 2H), 1.58 (m, 4H), 2.11 (s, 3H), 2.46 (m, 4H), 2.71 (t, J=5.8 Hz, 2H), 3.75 (s, 3H), 3.86 (s, 3H), 4.06 (t, J=5.8 Hz, 2H), 6.64 (d, J=8.9 Hz, 1H), 6.75 (d, J=8.6 Hz, 2H), 6.95 (d, J=8.9 Hz, 1H), 7.20 (s, 2H), 7.31 (s, 1H), 7.54 (d, J=8.9 Hz, 1H), 7.77 (d, J=8.6 Hz, 2H); 13C NMR d 16.4, 24.4, 26.1, 55.3, 55.6, 55.9, 57.9, 66.4, 104.8, 110.2, 114.5, 115.0, 124.3, 125.8, 127.1, 128.0, 130.6, 130.8, 131.6, 132.5, 134.3, 140.3, 143.2, 157.9, 158.3, 163.2, 193.6; MS (FD) m/e 515 (M+); Anal. calc'd. for C31H33NO4S: C, 72.21; H, 6.45; N, 2.72. Found: C, 72.43; H, 6.53; N, 2.95.

Aufarbeitung

  1. customto provide

Quellen und Nachweise

ORD-Eintrag
ord-7a49519a90594f86b0a53a663c4f5303
Quelldatensatz
uspto-grants-1999_12
Patentnummer
US05998442

Verknüpfte Notizen

Wird geladen…