Potassium Carbonate → (S)N-(1-Benzyl-6-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)-benzene-sulfonamide

HRID 1363093Notes

Reaction equation

HRID 1363093 reaction equation
[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14](Br)=[CH:15][CH:16]=2)[CH2:11][C@H: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.[C:29]1(B(O)O)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C([O-])([O-])=O.[K+].[K+]>C1COCC1.CO>[CH2:1]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[CH:15][CH:16]=2)[CH2:11][C@H: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

5

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic Acid3×HCID 11224878(S)-N-(1-Benzyl-6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

Product 1

HCID 11465214(S)N-(1-Benzyl-6-phenyl-1,2,3,4-tetrahydroquinolin-3-yl)-benzene-sulfonamideYield 51.5%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

The title compound was also prepared using the following procedures: To a solution of 87C (510 mg, 1.11 mmol) in THF/MeOH (2.1, 15 mL) was added phenylboronic acid (272 mg, 2.22 mmol), followed by K2CO3 (613 mg, 4.44 mmol) and PXPd (30 mg, 0.056 mmol). The reaction mixture was stirred at 60° C. for 2 h, then additional amount of phenylboronic acid (54 mg, 0.44 mmol) and PXPd (16 mg, 0.028 mmol) were added. After 2 h at 60° C., same amount of phenylboronic acid and PXPd were added again to the reaction mixture to push completion of the reaction. After stirring at 60° C. for one more hour, the reaction was allowed to cool to RT and concentrated. The residue was partitioned between water and CH2Cl2, and the aqueous phase extracted with CH2Cl2 (50 mL×2). The combined organics were washed with brine, dried (Na2SO4) and concentrated. The residue was purified using chromatography (silica gel) eluting with EtOAc/hexane (0-60%) to afford the title compound (260 mg, 51%) as a white solid.

Workup

  1. waitAfter 2 h at 60° C.
  2. customcompletion of the reaction
  3. stirringAfter stirring at 60° C. for one more hour
  4. temperatureto cool to RT
  5. concentrationconcentrated
  6. customThe residue was partitioned between water and CH2Cl2
  7. extractionthe aqueous phase extracted with CH2Cl2 (50 mL×2)
  8. washThe combined organics were washed with brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customThe residue was purified
  12. washeluting with EtOAc/hexane (0-60%)

Sources & evidence

ORD record
ord-8b467691cb1646af89d9e67c171b5d56
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

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