Triethylamine → 1-(5-Bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline

HRID 1891370Notes

Reaction equation

HRID 1891370 reaction equation
[Br:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([S:8](Cl)(=[O:10])=[O:9])[CH:7]=1.[CH3:14][C:15]1([CH3:25])[C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[NH:18][CH2:17][CH2:16]1.C(N(CC)CC)C.S(Cl)(Cl)(=O)=O>C(Cl)Cl>[Br:1][C:2]1[C:3]([Cl:13])=[CH:4][C:5]([F:12])=[C:6]([S:8]([N:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:15]([CH3:25])([CH3:14])[CH2:16][CH2:17]2)(=[O:10])=[O:9])[CH:7]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 24648Sulfuryl chlorideHCID 132194414,4-Dimethyl-1,2,3,4-tetrahydroquinolineHCID 566047345-Bromo-4-chloro-2-fluoro-benzenesulfonyl chloride

Product 1

HCID 684692731-(5-Bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinolineYield 89.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 5-bromo-4-chloro-2-fluorobenzenesulfonyl chloride (3.15 g, 10.8 mmol) in dry DCM (40 mL), was added 4,4-dimethyl-1,2,3,4-tetrahydro-quinoline (1.50 g, 9.3 mmol) and triethylamine (2.15 mL, 15.5 mmol). The mixture was stirred at ambient temperature for 16 hrs. Additional sulfonyl chloride (0.93 g, 3.2 mmole) was added and the mixture was stirred an additional 72 hrs. The mixture was washed with 1N hydrochloric acid solution, saturated sodium bicarbonate solution and brine. The organic layer was dried over MgSO4 and the filtrate evaporated. The residue was purified by silica gel chromatography [eluent: 5% ethyl acetate in hexane] to give 1-(5-bromo-4-chloro-2-fluoro-benzenesulfonyl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline as a yellow solid (3.6 g). tR=2.82 min (method 1).

Workup

  1. stirringthe mixture was stirred an additional 72 hrs
  2. washThe mixture was washed with 1N hydrochloric acid solution, saturated sodium bicarbonate solution and brine
  3. dry with materialThe organic layer was dried over MgSO4
  4. customthe filtrate evaporated
  5. customThe residue was purified by silica gel chromatography [eluent: 5% ethyl acetate in hexane]

Sources & evidence

ORD record
ord-8b6819cd73404dbdb71e1a7718c9a3d2
Source dataset
uspto-grants-2013_08
Patent number
US08507536B2

Reaction notes

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