6-Bromo-4-{4-[4-(methylsulfonyl)phenoxy]piperidino}quinoline → 4-[4-(4-methylsulfonylphenoxy)piperidin-1-yl]-6-(3-trifluoromethyl-1-trityl-1H-pyrazol-4-yl) quinoline
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][CH:6]=[C:5]2[N:12]1[CH2:17][CH2:16][CH:15]([O:18][C:19]2[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1.[F:29][C:30]([F:59])([F:58])[C:31]1[C:35](B(O)O)=[CH:34][N:33]([C:39]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[N:32]=1>>[CH3:28][S:25]([C:22]1[CH:23]=[CH:24][C:19]([O:18][CH:15]2[CH2:16][CH2:17][N:12]([C:5]3[C:4]4[C:9](=[CH:10][CH:11]=[C:2]([C:35]5[C:31]([C:30]([F:58])([F:59])[F:29])=[N:32][N:33]([C:39]([C:46]6[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=6)([C:52]6[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=6)[C:40]6[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=6)[CH:34]=5)[CH:3]=4)[N:8]=[CH:7][CH:6]=3)[CH2:13][CH2:14]2)=[CH:20][CH:21]=1)(=[O:27])=[O:26]Participants
3
Procedure
150 mg 6-bromo-4-{4-[4-(methylsulfonyl)phenoxy]piperidino}quinoline (compound in Production Example 89) and 180 mg 3-trifluoromethyl-1-trityl-1H-4-pyrazolylboronic acid (compound in Production Example 31) were reacted in the same manner as in Example 9, to give 244 mg 4-[4-(4-methylsulfonylphenoxy)piperidin-1-yl]-6-(3-trifluoromethyl-1-trityl-1H-pyrazol-4-yl) quinoline. This product was reacted in the same manner as in Example 67, to give 130 mg of the title compound as pale yellow crystals.
Sources & evidence
- ORD record
- ord-d3ecdb12e6c848a6abe3d00d7327c16f
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074801B1
Reaction notes
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