Methyl iodide → 6-Methoxy-1'-(4-methoxybenzyl)-2'-oxo-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile
Reaction equation
IC.Br[CH2:4]C1OC(C(F)(F)F)=CC=1.[OH:14][C:15]1[C:20]([C:21]#[N:22])=[CH:19][C:18]2[C:23]3([CH2:42][O:43][C:17]=2[CH:16]=1)[C:31]1[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=1)[N:25]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[C:24]3=[O:41].CC1C2C=C3C4(C5C(=CC=CC=5)NC4=O)COC3=CC=2ON=1>>[CH3:4][O:14][C:15]1[C:20]([C:21]#[N:22])=[CH:19][C:18]2[C:23]3([CH2:42][O:43][C:17]=2[CH:16]=1)[C:31]1[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=1)[N:25]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=1)[C:24]3=[O:41]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 9 and making non-critical variations using iodomethane to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, and 6-hydroxy-1′-(4-methoxybenzyl)-2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile to replace 3-methylspiro[furo[3,2-f][1,2]benzisoxazole-5,3′-indol]-2′(1′H)-one, 6-methoxy-1′-(4-methoxybenzyl)-2′-oxo-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile was obtained (62%): mp 207-208° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, CDCl3) δ 7.27-7.20 (m, 3H), 7.10-6.99 (m, 2H), 6.90-6.83 (m, 4H), 6.56 (s, 1H), 5.07-4.74 (m, 4H), 3.90 (s, 3H), 3.78 (s, 3H); MS (ES+) m/z 412.9 (M+1).
Sources & evidence
- ORD record
- ord-7a0cfebbac2b4ce3ace507466e7c3fe2
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
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