3-(Chloromethyl)-5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazole → 1'-({5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

HRID 645245Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 645245
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]2([C:13]3=[CH:14][C:15]4[O:19][CH2:18][O:17][C:16]=4[CH:20]=[C:12]3[O:11][CH2:10]2)[C:2]1=[O:21].BrC1C=CC=C2C=1C1(C3=CC4OCOC=4C=C3OC1)C(=O)N2.Cl[CH2:45][C:46]1[N:50]=[C:49]([C:51]2[CH:56]=[CH:55][C:54]([C:57]([F:60])([F:59])[F:58])=[CH:53][CH:52]=2)[O:48][N:47]=1.BrCC1OC(C(F)(F)F)=CC=1>>[F:60][C:57]([F:58])([F:59])[C:54]1[CH:53]=[CH:52][C:51]([C:49]2[O:48][N:47]=[C:46]([CH2:45][N:1]3[C:9]4[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=4)[C:3]4([C:13]5=[CH:14][C:15]6[O:19][CH2:18][O:17][C:16]=6[CH:20]=[C:12]5[O:11][CH2:10]4)[C:2]3=[O:21])[N:50]=2)=[CH:56][CH:55]=1

Komponenten

5

Edukt 4

HCID 27366243-(Chloromethyl)-5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazoleHCID 27946052-(Bromomethyl)-5-(trifluoromethyl)furanHCID 53375495spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-oneHCID 592633724'-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1H)-one

Produkt 1

HCID 592633901'-({5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)spiro[furo[2,3-f][1,3]benzodioxole-7,3'-indol]-2'(1'H)-one

Versuchsvorschrift

Following the procedure described in EXAMPLE 10.47, and making non-critical variations using spiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one to replace 4′-bromospiro[furo[2,3-f][1,3]benzodioxole-7,3′-indol]-2′(1′H)-one, and 3-chloromethyl-5-[4-(trifluoromethyl)phenyl]-1,2,4-oxadiazole to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, the title compound was obtained (44%): 1H NMR (300 MHz, CDCl3) δ 8.22 (d, 2H), 7.76 (d, 2H), 7.30-7.18 (m, 2H), 7.06 (t, 1H), 6.91 (d, 1H), 6.51 (s, 1H), 6.40 (s, 1H), 5.88 (s, 2H), 5.17 (ABq, 2H), 4.86 (ABq, 2H); MS (ES+) m/z 508.1 (M+1).

Quellen und Nachweise

ORD-Eintrag
ord-86ad4c7e57734c28a5ac6489f1560a88
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700641B2

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