4,4,5,5-Tetramethyl-2-(2-methylfuran-3-yl)-1,3,2-dioxaborolane → 2-Tert-butoxy-2-[4-(3,4-dimethylphenyl)-2-methyl-7-(2-methyl-3-furyl)-1-oxo-3-isoquinolyl]acetic acid
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.CC1(C)C(C)(C)OB([C:40]2[CH:44]=[CH:43][O:42][C:41]=2[CH3:45])O1>>[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]([C:40]1[CH:44]=[CH:43][O:42][C:41]=1[CH3:45])[CH:11]=2)[C:15]([OH:17])=[O:16])([CH3:21])[CH3:22]Participants
3
Reactant 2
Product 1
Procedure
The title compound was prepared in two steps in a manner similar to that described in Example 191 from methyl [7-bromo-4-(3,4-dimethylphenyl)-2-methyl-1-oxo-1,2-dihydro-3-isoquinolinyl][(1,1-dimethylethyl)oxy]acetate and 4,4,5,5-tetramethyl-2-(2-methyl-3-furanyl)-1,3,2-dioxaborolane and was isolated as a pale yellow solid (10 mg, 49%) after reverse phase chromatography: 1H NMR (400 MHz, CHLOROFORM-d) δ=8.58-8.46 (m, 1 H), 7.62-7.53 (m, 1 H), 7.46-7.33 (m, 2 H), 7.32-7.24 (m, 1 H), 7.24-7.05 (m, 2 H), 6.62 (t, J=1.9 Hz, 1 H), 5.37 (s, 1 H), 3.71 (d, J=1.2 Hz, 3 H), 2.51 (d, J=2.3 Hz, 3 H), 2.37 (d, J=1.2 Hz, 3 H), 2.33 (d, J=2.0 Hz, 3 H), 1.09 (d, J=4.5 Hz, 9 H); LC/MS (m/z) ES+=474 (M+1).
Sources & evidence
- ORD record
- ord-17e3fec5da8040cb86edf4eae53a5aea
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029391B2
Reaction notes
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