1-Iodopentane → 4'-bromo-1'-pentyl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3'-indol]-2'(1H)-one
Reaktionsgleichung
I[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].BrCC1OC(C(F)(F)F)=CC=1.[Br:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[C:21]1([C:40]3[C:31](=[CH:32][C:33]4[O:38][CH2:37][CH2:36][O:35][C:34]=4[CH:39]=3)[O:30][CH2:29]1)[C:22](=[O:28])[NH:23]2.CC1C2C=C3C4(C5C(=CC=CC=5)NC4=O)COC3=CC=2ON=1>>[Br:18][C:19]1[CH:27]=[CH:26][CH:25]=[C:24]2[C:20]=1[C:21]1([C:40]3[C:31](=[CH:32][C:33]4[O:38][CH2:37][CH2:36][O:35][C:34]=4[CH:39]=3)[O:30][CH2:29]1)[C:22](=[O:28])[N:23]2[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]Komponenten
Edukt 4
Produkt 1
Versuchsvorschrift
Following the procedure as described in EXAMPLE 9 and making non-critical variations using 1-iodopentane to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, and 4′-bromo-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one to replace 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1′H)-one, 4′-bromo-1′-pentyl-2,3-dihydrospiro[furo[2,3-g][1,4]benzodioxine-8,3′-indol]-2′(1′H)-one was obtained (54%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ 7.20-7.15 (m, 2H), 6.87-6.83 (m, 1H), 6.45 (s, 1H), 6.16 (s, 1H), 4.89 (ABq, 2H), 4.20-4.11 (m, 4H), 3.85-3.59 (m, 2H), 1.72-1.67 (m, 2H), 1.38-1.25 (m, 4H), 0.92-0.85 (m, 3H); 13C NMR (75 MHz, CDCl3). δ 117.0, 156.4, 144.7, 144.5, 137.9, 130.13, 130.10, 126.9, 119.9, 118.1, 111.0, 107.5, 98.9, 76.8, 64.4, 63.8, 59.3, 40.5, 28.9, 27.0, 22.3, 13.9; MS (ES+) m/z 443.9 (M+1), 445.9 (M+1).
Quellen und Nachweise
- ORD-Eintrag
- ord-948531edbe0343db943e862de6559443
- Quelldatensatz
- uspto-grants-2013_04
- Patentnummer
- US08415370B2
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