Potassium Carbonate → N-(1-Benzyl-6-(4-fluorophenyl)-1,2,3,4-tetrahydroquinolin-3-yl)benzenesulfonamide

HRID 1363094Notes

Reaction equation

HRID 1363094 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14](Br)=[CH:15][CH:16]=2)[CH2:11][CH:10]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.CO.C1COCC1.C([O-])([O-])=O.[K+].[K+]>O>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:33]3[CH:34]=[CH:35][C:30]([F:29])=[CH:31][CH:32]=3)=[CH:15][CH:16]=2)[CH2:11][CH:10]([NH:19][S:20]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 21899815MeOH tetrahydrofuranHCID 59778201N-(1-benzyl-6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

Product 1

HCID 59778143N-(1-Benzyl-6-(4-fluorophenyl)-1,2,3,4-tetrahydroquinolin-3-yl)benzenesulfonamideYield 79%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 87B (3.648 g, 8.0 mmol) and 4-fluorobenzene boronic acid (2.24 g, 16.0 mmol) in a mixed solvent of MeOH-THF (80 mL, 1:1 ratio) was added K2CO3 (4.423 g, 32.0 mmol), followed by PXPd (215 mg, 0.40 mmol). The resulting suspension was vigorously stirred in a 70° oil bath for 35 min. After cooling down to RT, the dark brown solution was diluted with water (200 mL), and extracted with EtOAc (200 mL×2). The combined EtOAc extracts were washed with brine, dried (Na2SO4) and concentrated. The residue was chromatographed (silica gel) eluting with EtOAc/hexane (0-30%) to afford the title compound (2.977 g, 79%) as a light brown solid.

Workup

  1. extractionextracted with EtOAc (200 mL×2)
  2. washThe combined EtOAc extracts were washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was chromatographed (silica gel)
  6. washeluting with EtOAc/hexane (0-30%)

Sources & evidence

ORD record
ord-e3075594254c4618a86e374ea1a9f7a7
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

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