6-Bromo-4-[4-(4-trifluoromethylsulfonylphenoxy)piperidin-1-yl] quinoline → 4-[4-(4-trifluoromethylsulfonylphenoxy)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]([C:28]([F:31])([F:30])[F:29])(=[O:27])=[O:26])=[CH:21][CH:20]=2)[CH2:14][CH2:13]1.[F:32][C:33]([F:62])([F:61])[C:34]1[C:38](B(O)O)=[CH:37][N:36]([C:42]([C:55]2[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=2)([C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)[C:43]2[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=2)[N:35]=1>>[F:30][C:28]([F:29])([F:31])[S:25]([C:22]1[CH:21]=[CH:20][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:38]5[C:34]([C:33]([F:61])([F:62])[F:32])=[N:35][N:36]([C:42]([C:49]6[CH:50]=[CH:51][CH:52]=[CH:53][CH:54]=6)([C:55]6[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=6)[C:43]6[CH:44]=[CH:45][CH:46]=[CH:47][CH:48]=6)[CH:37]=5)[CH:3]=4)[N:8]=[CH:7][CH:6]=3)[CH2:13][CH2:14]2)=[CH:24][CH:23]=1)(=[O:26])=[O:27]Participants
3
Reactant 2
Product 1
Procedure
150 mg 6-bromo-4-[4-(4-trifluoromethylsulfonylphenoxy)piperidin-1-yl] quinoline (compound in Production Example 456) and 160 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 221 mg 4-[4-(4-trifluoromethylsulfonylphenoxy)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 106 mg of the title compound as colorless crystals.
Sources & evidence
- ORD record
- ord-7fd3e3361f044fe8b4dc8cf3fe2067c6
- Source dataset
- uspto-grants-2006_07
- Patent number
- US07074801B1
Reaction notes
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