2-(Bromomethyl)pyridine hydrobromide → 6-Fluoro-2'-oxo-1'-(pyridin-2-ylmethyl)-1',2'-dihydrospiro[1-benzofuran-3,3'-indole]-5-carbonitrile
Reaction equation
Br.Br[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.BrCC1OC(C(F)(F)F)=CC=1.[F:21][C:22]1[C:27]([C:28]#[N:29])=[CH:26][C:25]2[C:30]3([CH2:40][O:41][C:24]=2[CH:23]=1)[C:38]1[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=1)[NH:32][C:31]3=[O:39].CC1C2C=C3C4(C5C(=CC=CC=5)NC4=O)COC3=CC=2ON=1>>[F:21][C:22]1[C:27]([C:28]#[N:29])=[CH:26][C:25]2[C:30]3([CH2:40][O:41][C:24]=2[CH:23]=1)[C:38]1[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=1)[N:32]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1)[C:31]3=[O:39]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in EXAMPLE 9 and making non-critical variations using 2-(bromomethyl)pyridine hydrobromide 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′-(pyridin-2-ylmethyl)-1′,2′-dihydrospiro[1-benzofuran-3,3′-indole]-5-carbonitrile was obtained (55%): mp 108-109° C.; 1H NMR (300 MHz, DMSO-d6) δ 7.71-7.66 (m, 1H), 7.29-7.20 (m, 3H), 7.15-7.03 (m, 3H), 6.93-6.90 (m, 1H), 6.79-6.76 (m, 1H), 5.26-4.85 (m, 4H); MS (ES+) m/z 371.9 (M+1).
Sources & evidence
- ORD record
- ord-935ba08cc35e42a09aab414a35c43d81
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
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