Diisopropylethylamine → 3-[4-(1-Methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidin-1-yl]quinoline

HRID 1873858Notes

Reaction equation

HRID 1873858 reaction equation
[CH3:1][C:2]([CH:17]1[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1)([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:16])([F:15])[F:14])[CH:8]=1)(=[O:6])=[O:5])[CH3:3].[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[C:25](B(O)O)[CH:24]=1.C(N(C(C)C)CC)(C)C>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.O1CCCC1>[CH3:3][C:2]([CH:17]1[CH2:22][CH2:21][N:20]([C:25]2[CH:24]=[N:23][C:32]3[C:27]([CH:26]=2)=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH2:19][CH2:18]1)([S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]([F:14])([F:16])[F:15])[CH:8]=1)(=[O:5])=[O:6])[CH3:1]

Participants

6

Reactant 3

HCID 81531DiisopropylethylamineHCID 2734663Quinoline-3-boronic acidHCID 594474094-(1-Methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine

Product 1

HCID 594471983-[4-(1-Methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidin-1-yl]quinolineYield 58.3%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a 10 ml vial was added 4-(1-methyl-1-{[3-(trifluoromethyl)phenyl]sulfonyl}ethyl)piperidine (30 mg, 0.089 mmol), quinolin-3-ylboronic acid (62 mg, 0.358 mmol), copper acetate (32.5 mg, 0.179 mmol), diisopropylethyl amine (0.049 ml, 0.358 mmol) and 1 ml tetrahydrofuran. The resulting reaction mixture was stirred at room temperature for one hour then 60° C. 3 hours. After aqueous work up, the crude product was purified on reverse phase column eluted with water/acetonitrile gradient solvent to give 24 mg desired product as fluffy white solid after lyophilizing.

Workup

  1. customThe resulting reaction mixture
  2. custom60° C
  3. custom3 hours
  4. customAfter aqueous work up, the crude product was purified on reverse phase column
  5. washeluted with water/acetonitrile gradient solvent

Sources & evidence

ORD record
ord-7e8707d0168247b0abf035f3b1797b07
Source dataset
uspto-grants-2012_11
Patent number
US08304434B2

Reaction notes

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