3-Fluorobenzenesulfonyl Chloride → HCID 56966431, compound

HRID 1036978Notes

Reaction equation

HRID 1036978 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([NH2:18])[CH:15]=[CH:16][CH:17]=1)[CH2:6][C:5]2([CH3:20])[CH3:19].[F:21][C:22]1[CH:23]=[C:24]([S:28](Cl)(=[O:30])=[O:29])[CH:25]=[CH:26][CH:27]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([C:12]1[CH:13]=[C:14]([NH:18][S:28]([C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([F:21])[CH:23]=3)(=[O:30])=[O:29])[CH:15]=[CH:16][CH:17]=1)[CH2:6][C:5]2([CH3:20])[CH3:19]

Participants

4

Reactant 2

HCID 27342583-Fluorobenzenesulfonyl ChlorideHCID 67290361HCID 67290361, compound

Product 1

HCID 56966431HCID 56966431, compoundYield 51.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

3-(6-Chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenylamine (150 mg, 0.53 mmol) and 3-fluoro-benzenesulfonyl chloride (92 mg, 0.63 mmol) were dissolved in pyridine (5 ml). The mixture was stirred at room temperature overnight. The solvent was removed and the residue was purified on column chromatography using petroleum ether/ethyl acetate=5:1 as eluent to afford N-[3-(6-chloro-4,4-dimethyl-1,2,3,4-tetrahydro-quinolin-2-yl)-phenyl]-3-fluoro-benzenesulfonamide 122 mg (yield: 41%) as yellow solid. MS (ESI+APCI) M+1=445.1.

Workup

  1. customThe solvent was removed
  2. customthe residue was purified on column chromatography

Sources & evidence

ORD record
ord-7071d79d991240808346473e145033f1
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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