2-Methylpyridine → 3-Hydroxy-5-methyl-1-phenethyl-3-(pyridin-2-ylmethyl)indolin-2-one
Reaction equation
Br[C:2]1[C:3]([CH2:8][C:9]2([OH:25])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=3)[N:11]([CH2:19][CH2:20][CH:21]([CH3:23])[CH3:22])[C:10]2=[O:24])=[N:4][CH:5]=[CH:6][CH:7]=1.[CH3:26][C:27]1C=C2C(=C[CH:35]=1)N(CCC1C=CC=CC=1)C(=O)C2=O.CC1C=CC=CN=1>>[OH:25][C:9]1([CH2:8][C:3]2[CH:2]=[CH:7][CH:6]=[CH:5][N:4]=2)[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([CH3:18])[CH:16]=2)[N:11]([CH2:19][CH2:20][C:21]2[CH:23]=[CH:35][CH:27]=[CH:26][CH:22]=2)[C:10]1=[O:24]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 2-methylpyridine (purchased from Fisher Scientific). 1H-NMR δ 8.6 (d, 1H), 7.65 (m, 1H), 7.27 (m, 6H), 7.05 (d, 1H), 6.98 (d, 1H), 6.71 (m, 2H), 4.6 (bs, OH), 3.5 (m, 1H), 3.8 (m, 1H), 3.1 (m, 2H), 2.95 (m, 2H), 2.21 (s, 3H). Calculated mass for C23H22N2O2, 358.17. Observed 359.1 (M+1).
Sources & evidence
- ORD record
- ord-143176ef7d5f4746b872c3467bb7f7f6
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079853B2
Reaction notes
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