6-Bromo-4-[4-(2-methylsulfonylphenoxy)-piperidin-1-yl] quinoline → 4-[4-(2-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][CH:22]=[CH:21][C:20]=2[S:25]([CH3:28])(=[O:27])=[O:26])[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:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[O:18][CH:15]1[CH2:16][CH2:17][N:12]([C:5]2[C:4]3[C:9](=[CH:10][CH:11]=[C:2]([C:35]4[C:31]([C:30]([F:58])([F:59])[F:29])=[N:32][N:33]([C:39]([C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)([C:52]5[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=5)[C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=5)[CH:34]=4)[CH:3]=3)[N:8]=[CH:7][CH:6]=2)[CH2:13][CH2:14]1)(=[O:27])=[O:26]Participants
3
Procedure
80 mg 6-bromo-4-[4-(2-methylsulfonylphenoxy)-piperidin-1-yl] quinoline (compound in Production Example 222) and 95 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 124 mg 4-[4-(2-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 70 mg of the title compound as colorless crystals.
Sources & evidence
- ORD record
- ord-ae4eadedae4b473b8faa9d7438f2e2d0
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074801B1
Reaction notes
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