6-Bromo-4-{4-[4-(methylsulfonyl)phenoxy]piperidino}quinoline → 4-[4-(4-methylsulfonylphenoxy)piperidin-1-yl]-6-(1-trityl-1H-pyrazol-4-yl) quinoline

HRID 1792624Notes

Reaction equation

HRID 1792624 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.[C:29]([N:48]1[CH:52]=[C:51](B(O)O)[CH:50]=[N:49]1)([C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1)([C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=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:51]5[CH:50]=[N:49][N:48]([C:29]([C:36]6[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=6)([C:30]6[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=6)[C:42]6[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=6)[CH:52]=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

Reactant 2

HCID 220311826-Bromo-4-{4-[4-(methylsulfonyl)phenoxy]piperidino}quinolineHCID 22031737(1-Trityl-1H-pyrazol-4-yl)boronic acid

Product 1

HCID 688153364-[4-(4-methylsulfonylphenoxy)piperidin-1-yl]-6-(1-trityl-1H-pyrazol-4-yl) quinolineYield 85.1%

Procedure

80 mg 6-bromo-4-{4-[4-(methylsulfonyl)phenoxy]piperidino}quinoline (compound in Production Example 89) and 80 mg 1-trityl-1H-4-pyrazolylboronic acid were reacted in the same manner as in Example 9, to give 102 mg 4-[4-(4-methylsulfonylphenoxy)piperidin-1-yl]-6-(1-trityl-1H-pyrazol-4-yl) quinoline. This product was reacted in the same manner as in Example 67, to give 52 mg of the title compound as colorless crystals.

Sources & evidence

ORD record
ord-2b28712309c345969b84f57b5b4ee487
Source dataset
uspto-grants-2006_07
Patent number
US07074801B1

Reaction notes

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