Pyridine → HCID 56966204, compound

HRID 1036953Notes

Reaction equation

HRID 1036953 reaction equation
[CH3:1][C:2]1([CH3:20])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=2)[NH:5][CH:4]([C:13]2[CH:14]=[C:15]([NH2:19])[CH:16]=[CH:17][CH:18]=2)[CH2:3]1.N1C=CC=CC=1.[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34](Cl)(=[O:36])=[O:35]>ClCCl>[F:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[S:34]([NH:19][C:15]1[CH:16]=[CH:17][CH:18]=[C:13]([CH:4]2[CH2:3][C:2]([CH3:20])([CH3:1])[C:11]3[C:6](=[CH:7][CH:8]=[C:9]([CH3:12])[CH:10]=3)[NH:5]2)[CH:14]=1)(=[O:36])=[O:35]

Participants

5

Reactant 3

HCID 1049PyridineHCID 1377612-Fluorobenzenesulphonyl chlorideHCID 672908283-(4,4,6-Trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine

Product 1

HCID 56966204HCID 56966204, compoundYield 47.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a stirred mixture of 3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (135 mg, 0.5 mmol) in dichloromethane (3 mL) was added pyridine (60 mg, 0.75 mmol) in dichloromethane (2 mL) and 2-fluoro-benzenesulfonyl chloride (108 mg, 0.56 mmol) under nitrogen. The resultant mixture was stirred for 4 h. The reaction mixture was diluted with dichloromethane, washed with water (twice), saturated brine, and dried over magnesium sulfate. Magnesium sulfate was removed by filtration, and after evaporation, the residue was purified on chromatography column (silica gel, petroleum ether:ethyl acetate=15:1) to afford 100 mg of 2-fluoro-N-[3-(4,4,6-trimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-benzenesulfonamide yellow solid (Yield: 47%). MS (ESI+APCI) M+1=425.2.

Workup

  1. washwashed with water (twice), saturated brine
  2. dry with materialdried over magnesium sulfate
  3. customMagnesium sulfate was removed by filtration
  4. customafter evaporation
  5. customthe residue was purified on chromatography column (silica gel, petroleum ether:ethyl acetate=15:1)

Sources & evidence

ORD record
ord-f809e66475044f76aa480278d2f9870c
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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