3-Bromophenol → 3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-4,5-dimethoxy-1-{[5-(trifluoromethyl)furan-2-yl]methyl}-1,3-dihydro-2H-indol-2-one
Reaction equation
[O:1]1[CH2:6][CH2:5][O:4][C:3]2[CH:7]=[C:8]([OH:11])[CH:9]=[CH:10][C:2]1=2.BrC1C=C(O)C=CC=1.[CH3:20][O:21][C:22]1[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[C:27]2[C:23]=1[C:24](=[O:44])[C:25](=[O:43])[N:26]2[CH2:33][C:34]1[O:35][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:38]=1.FC(F)(F)C1OC(CN2C3C(=CC=CC=3)C(=O)C2=O)=CC=1>>[OH:44][C:24]1([C:9]2[C:8]([OH:11])=[CH:7][C:3]3[O:4][CH2:5][CH2:6][O:1][C:2]=3[CH:10]=2)[C:23]2[C:27](=[CH:28][CH:29]=[C:30]([O:31][CH3:32])[C:22]=2[O:21][CH3:20])[N:26]([CH2:33][C:34]2[O:35][C:36]([C:39]([F:41])([F:40])[F:42])=[CH:37][CH:38]=2)[C:25]1=[O:43]Participants
5
Reactant 4
Product 1
Procedure
Following the procedure as described in PREPARATION 2A and making non-critical variations using 2,3-dihydrobenzo[b][1,4]dioxin-6-ol to replace 3-bromophenol, and 4,5-dimethoxy-1-{[5-(trifluoromethyl)furan-2-yl]methyl}-1H-indole-2,3-dione to replace 1-((5-(trifluoromethyl)furan-2-yl)methyl)indoline-2,3-dione, 3-hydroxy-3-(7-hydroxy-2,3-dihydro-1,4-benzodioxin-6-yl)-4,5-dimethoxy-1-{[5-(trifluoromethyl)furan-2-yl]methyl}-1,3-dihydro-2H-indol-2-one was obtained (67%) as a colorless solid: 1H NMR (300 MHz, CDCl3) δ8.59 (s, 1H), 6.88 (d, J=8.4 Hz, 1H), 6.71-6.65 (m, 1H), 6.61 (d, J=8.4 Hz, 1H), 6.54 (s, 1H), 6.33-6.25 (m, 2H), 4.89-4.71 (m, 2H), 4.25-4.02 (m, 4H), 3.99 (s, 1H), 3.83 (s, 6H).
Sources & evidence
- ORD record
- ord-68da096e7c8a4fb9a4f26ab53322b738
- Source dataset
- uspto-grants-2012_09
- Patent number
- US08263606B2
Reaction notes
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