Trifluoroacetate → 2-Tert-butoxy-2-[4-(3,4-dimethylphenyl)-2-methyl-7-(1-methylpyrazol-4-yl)-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.[CH3:32][N:33]1[CH:37]=[C:36](B2OC(C)(C)C(C)(C)O2)[CH:35]=[N:34]1.FC(F)(F)C([O-])=O>>[CH3:22][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:36]1[CH:35]=[N:34][N:33]([CH3:32])[CH:37]=1)[CH:11]=2)[C:15]([OH:17])=[O:16])([CH3:21])[CH3:23]Participants
4
Reactant 3
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 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and was isolated as a pale yellow solid (20 mg, 57%) after reverse phase chromatography as the trifluoroacetate salt: 1H NMR (400 MHz, CHLOROFORM-d) δ=8.59 (s, 1 H), 7.91 (s, 1 H), 7.82 (s, 1 H), 7.70-7.53 (m, 1 H), 7.45-7.31 (m, 1 H), 7.32-7.22 (m, 1 H), 7.17 (dd, J=8.5, 12.4 Hz, 1 H), 7.12-7.03 (m, 1 H), 5.36 (d, J=1.0 Hz, 1 H), 4.00 (s, 3 H), 3.73 (s, 3 H), 2.38 (s, 3 H), 2.33 (d, J=2.5 Hz, 3 H), 1.07 (d, 9 H); LC/MS (m/z) ES+=474 (M+1).
Sources & evidence
- ORD record
- ord-c2c6fc7493ee4adb9e88277ac466638b
- Source dataset
- uspto-grants-2015_05
- Patent number
- US09029391B2
Reaction notes
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