Reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([C:24]3[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH3:31])[CH:25]=3)=[C:7]([CH:14]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:15]([O:17]C)=[O:16])[N:8]([CH3:13])[C:9]2=[O:12])=[CH:4][CH:3]=1.[Br-].[CH2:33]([Zn+])[CH:34]([CH3:36])[CH3:35]>>[CH3:23][C:20]([O:19][CH:14]([C:7]1[N:8]([CH3:13])[C:9](=[O:12])[C:10]2[C:5]([C:6]=1[C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[C:26]([CH3:31])[CH:25]=1)=[CH:4][CH:3]=[C:2]([CH2:33][CH:34]([CH3:36])[CH3:35])[CH:11]=2)[C:15]([OH:17])=[O:16])([CH3:21])[CH3:22]Participants
3
Procedure
The title compound was prepared in two steps in a manner similar to that described in Example 171 from methyl 2-(7-bromo-4-(3,4-dimethylphenyl)-2-methyl-1-oxo-1,2-dihydroisoquinolin-3-yl)-2-(tert-butoxy)acetate and isobutylzinc(II) bromide and was isolated as a white solid (11.7 mg, 37%) after reverse phase chromatography: 1H NMR (400 MHz, CHLOROFORM-d) δ=8.27 (s, 1 H), 7.42-7.22 (m, 3 H), 7.16-7.00 (m, 2 H), 5.35 (m, 1 H), 3.70 (s, 3 H), 2.61 (m, 2 H), 2.36 (m, 3 H), 2.32 (m, 3 H), 2.00-1.85 (m, 1 H), 1.07 (m, 9 H), 0.96-0.85 (m, 6 H); LC/MS (m/z) ES+=450 (M+1).
Sources & evidence
- ORD record
- ord-14d7f769988743179b6999bbe4e40a94
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029391B2
Linked notes
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