6-Bromo-4-[4-(4-trifluoromethylsulfonylphenoxy)piperidin-1-yl] quinoline → 6-(1-trityl-1H-pyrazol-4-yl)-4-[4-(4-trifluoromethylsulfonylphenoxy)piperidin-1-yl] quinoline

HRID 1792628Notes

Reaction equation

HRID 1792628 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.[C:32]([N:51]1[CH:55]=[C:54](B(O)O)[CH:53]=[N:52]1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1>>[C:32]([N:51]1[CH:55]=[C:54]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[N:8]=[CH:7][CH:6]=[C:5]3[N:12]2[CH2:17][CH2:16][CH:15]([O:18][C:19]3[CH:20]=[CH:21][C:22]([S:25]([C:28]([F:29])([F:31])[F:30])(=[O:26])=[O:27])=[CH:23][CH:24]=3)[CH2:14][CH2:13]2)[CH:53]=[N:52]1)([C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)([C:45]1[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=1)[C:33]1[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=1

Participants

3

Reactant 2

HCID 220317286-Bromo-4-[4-(4-trifluoromethylsulfonylphenoxy)piperidin-1-yl] quinolineHCID 22031737(1-Trityl-1H-pyrazol-4-yl)boronic acid

Product 1

HCID 220315206-(1-trityl-1H-pyrazol-4-yl)-4-[4-(4-trifluoromethylsulfonylphenoxy)piperidin-1-yl] quinolineYield 94.6%

Procedure

150 mg 6-bromo-4-[4-(4-trifluoromethylsulfonylphenoxy)piperidin-1-yl] quinoline (compound in Production Example 456) and 134 mg 1-trityl-1H-4-pyrazolylboronic acid were reacted in the same manner as in Example 9, to give 205 mg 6-(1-trityl-1H-pyrazol-4-yl)-4-[4-(4-trifluoromethylsulfonylphenoxy)piperidin-1-yl] quinoline. This product was reacted in the same manner as in Example 67, to give 90 mg of the title compound as pale yellow crystals.

Sources & evidence

ORD record
ord-56e412bd410441dda3c53c6e36267bd4
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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