Bromopinacolone → 1-(3-isobutyryl-6-methoxy-1H-indazol-1-yl)-3,3-dimethylbutan-2-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([C:12](=[O:16])[CH:13]([CH3:15])[CH3:14])=[N:8][NH:9]2)=[CH:5][CH:4]=1.Br[CH2:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21]>>[C:12]([C:7]1[C:6]2[C:10](=[CH:11][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:9]([CH2:18][C:19](=[O:24])[C:20]([CH3:23])([CH3:22])[CH3:21])[N:8]=1)(=[O:16])[CH:13]([CH3:14])[CH3:15]Participants
3
Procedure
Reaction of 1-(6-methoxy-1H-indazol-3-yl)-2-methylpropan-1-one with 1-bromo-3,3-dimethylbutan-2-one using a procedure similar to that described in Example 3 Step A gave the title compound. Recrystallization from 2:1 hexanes and EtOAc gave fine needles. 1H NMR (CDCl3, 500 MHz) δ 8.25 (d, 8.9 Hz, 1H), 6.98 (dd, 2.0 & 8.9 Hz, 1H), 6.52 (d, 1.8 Hz, 1H), 5.37 (s, 2H), 3.87 (s, 3H), 3.86 (heptet, 6.9 Hz, 1H), 1.36 (s, 9H), 1.27 (d, 6.8 Hz, 6H). LC-MS: 3.70 min. (m/Z=317.1, 339.1).
Sources & evidence
- ORD record
- ord-1104d82efef94ad2b3644cffe1dfb9af
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07563816B2
Reaction notes
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