Reaction equation
Br[C:2]1[CH:11]=[CH:10][C:9]2[N:8]=[CH:7][C:6]3[N:12]([CH3:24])[C:13](=[O:23])[N:14]([C:15]4[C:16]([CH3:22])=[N:17][N:18]([CH2:20][CH3:21])[CH:19]=4)[C:5]=3[C:4]=2[CH:3]=1.[CH2:25]([O:27][C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][C:29]=1[O:43][CH3:44])[CH3:26]>>[CH2:25]([O:27][C:28]1[CH:33]=[CH:32][C:31]([C:2]2[CH:11]=[CH:10][C:9]3[N:8]=[CH:7][C:6]4[N:12]([CH3:24])[C:13](=[O:23])[N:14]([C:15]5[C:16]([CH3:22])=[N:17][N:18]([CH2:20][CH3:21])[CH:19]=5)[C:5]=4[C:4]=3[CH:3]=2)=[CH:30][C:29]=1[O:43][CH3:44])[CH3:26]Participants
3
Reactant 2
Product 1
Procedure
The title compound was synthesized in a similar manner as described for Example 1.1 using 8-bromo-1-(1-ethyl-3-methyl-1H-pyrazol-4-yl)-3-methyl-1,3-dihydro-imidazo[4,5-c]quinolin-2-one (Intermediate F, 39 mg, 0.100 mmol) and 2-(4-ethoxy-3-methoxy-phenyl)-4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (Stage 29.1.1, 34 mg, 0.123 mmol) to give the title compound as a white solid. (HPLC: tR 2.88 min (Method A); M+H=458 MS-ES; 1H-NMR (d6-DMSO, 400 MHz) 8.92 (s, 1H), 8.16 (s, 1H), 8.07-8.02 (m, 1H), 7.94-7.88 (m, 1H), 7.51-7.47 (m, 1H), 7.06-6.96 (m, 3H), 4.20-4.12 (m, 2H), 4.06-3.98 (m, 2H), 3.85 (s, 3H), 3.57 (s, 3H), 1.97 (s, 3H), 1.42-1.29 (m, 6H))
Workup
- customThe title compound was synthesized in a similar manner
Sources & evidence
- ORD record
- ord-102da3a103314ee3a6cabbc311fdc4a9
- Source dataset
- uspto-grants-2013_07
- Patent number
- US08476294B2
Linked notes
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