5-Methyl-1-phenethylindoline-2,3-dione → 3-Hydroxy-3-((5-methoxypyridin-2-yl)methyl)-5-methyl-1-phenethylindolin-2-one
Reaction equation
BrC1C(CC2(O)C3C(=CC=C(C)C=3)N(CCC(C)C)C2=O)=NC=CC=1.[CH3:26][C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[N:32]([CH2:36][CH2:37][C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)[C:31](=[O:44])[C:30]2=[O:45].[CH3:46][O:47][C:48]1[CH:49]=[CH:50][C:51]([CH3:54])=[N:52][CH:53]=1>>[OH:45][C:30]1([CH2:54][C:51]2[CH:50]=[CH:49][C:48]([O:47][CH3:46])=[CH:53][N:52]=2)[C:29]2[C:33](=[CH:34][CH:35]=[C:27]([CH3:26])[CH:28]=2)[N:32]([CH2:36][CH2:37][C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:31]1=[O:44]Participants
4
Procedure
This compound was prepared in an analogous manner to 3-((3-bromopyridin-2-yl)methyl)-3-hydroxy-1-isopentyl-5-methylindolin-2-one using 5-methyl-1-phenethylindoline-2,3-dione and 5-methoxy-2-methylpyridine (purchased from Aldrich). 1H-NMR δ 8.29 (d, 1H), 7.34 (m, 2H), 7.25 (m, 3H), 7.18 (dd, 1H), 7.07 (dd, 1H), 6.90 (d, 1H), 6.80 (s, 1H), 6.71 (d, 1H), 5.3 (bs, OH), 3.98 (dt, 1H), 3.91 (s, 3H), 3.81 (dt, 1H), 3.05 (d, 2H), 2.97 (t, 2H), 2.27 (s, 3H). Calculated mass for C24H24N2O3, 388.18. Observed 389.2 (M+1).
Sources & evidence
- ORD record
- ord-0a45474d87cb4f0298a448d079c65705
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079853B2
Reaction notes
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