2-(Bromomethyl)-5-(trifluoromethyl)furan → 6-fluoro-2'-oxo-1'-[(2R)-tetrahydrofuran-2-ylmethyl]-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile
Reaction equation
CC1C=CC(S(O[CH2:12][C@H:13]2[CH2:17][CH2:16][CH2:15][O:14]2)(=O)=O)=CC=1.BrCC1OC(C(F)(F)F)=CC=1.[F:29][C:30]1[C:35]([C:36]#[N:37])=[CH:34][C:33]2[C:38]3([CH2:48][O:49][C:32]=2[CH:31]=1)[C:46]1[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=1)[NH:40][C:39]3=[O:47].CC1C2C=C3C4(C5C(=CC=CC=5)NC4=O)COC3=CC=2ON=1>>[F:29][C:30]1[C:35]([C:36]#[N:37])=[CH:34][C:33]2[C:38]3([CH2:48][O:49][C:32]=2[CH:31]=1)[C:46]1[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=1)[N:40]([CH2:12][C@H:13]1[CH2:17][CH2:16][CH2:15][O:14]1)[C:39]3=[O:47]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 9 and making non-critical variations using (R)-(tetrahydrofuran-2-yl)methyl 4-methylbenzenesulfonate 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′-[(2R)-tetrahydrofuran-2-ylmethyl]-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile was obtained (34%): 1H NMR (300 MHz, CDCl3) δ 7.37-7.27 (m, 1H), 7.12-7.06 (m, 3H), 7.01-6.92 (m, 1H), 6.79-6.74 (m, 1H), 4.94 (ABq, 2H), 4.31-4.21 (m, 1H), 3.91-3.72 (m, 4H), 2.12-1.84 (m, 4H); MS (ES+) m/z 364.9 (M+1).
Sources & evidence
- ORD record
- ord-8ac47385a7d043abb5dacde31b529e31
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
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