2-(Bromomethyl)-5-(trifluoromethyl)furan → 6-fluoro-2'-oxo-1'-[[3-(trifluoromethyl)pyridin-2-yl]methyl]spiro[2H-1-benzofuran-3,3'-indole]-5-carbonitrile
Reaction equation
Cl[CH2:2][C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][N:4]=1.BrCC1OC(C(F)(F)F)=CC=1.[F:24][C:25]1[C:30]([C:31]#[N:32])=[CH:29][C:28]2[C:33]3([CH2:43][O:44][C:27]=2[CH:26]=1)[C:41]1[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=1)[NH:35][C:34]3=[O:42].CC1C2C=C3C4(C5C(=CC=CC=5)NC4=O)COC3=CC=2ON=1>>[F:24][C:25]1[C:30]([C:31]#[N:32])=[CH:29][C:28]2[C:33]3([CH2:43][O:44][C:27]=2[CH:26]=1)[C:41]1[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=1)[N:35]([CH2:2][C:3]1[C:8]([C:9]([F:12])([F:11])[F:10])=[CH:7][CH:6]=[CH:5][N:4]=1)[C:34]3=[O:42]Participants
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 9 and making non-critical variations using 2-(chloromethyl)-3-(trifluoromethyl)pyridine to replace 2-(bromomethyl)-5-(trifluoromethyl)furan, and 6-fluoro-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-fluoro-2′-oxo-1′-{[3-(trifluoromethyl)pyridin-2-yl]methyl}-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile was obtained (67%): mp 209-211° C. (ethyl acetate/hexanes); 1H NMR (300 MHz, DMSO-d6) δ 8.65 (d, J=6.0 Hz, 1H), 8.23 (d, J=6.0 Hz, 1H), 7.58-7.54 (m, 1H), 7.42-7.40 (m, 1H), 7.31-7.23 (m, 3H), 7.06-7.01 (m, 1H), 6.93-6.91 (m, 1H), 5.21 (s, 2H), 5.03 (s, 2H); MS (ES+) m/z 440.2 (M+1).
Sources & evidence
- ORD record
- ord-9ddf0f8d16d04158a57ea9cbafbb48eb
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08916580B2
Reaction notes
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