2-Fluorobenzenesulphonyl chloride → HCID 56966428, compound

HRID 1036975Notes

Reaction equation

HRID 1036975 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:27]=[CH:26][CH:25]=[CH:24][C:23]=1[S:28](Cl)(=[O:30])=[O:29]>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:23]3[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=3[F:21])(=[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 1377612-Fluorobenzenesulphonyl chlorideHCID 67290361HCID 67290361, compound

Product 1

HCID 56966428HCID 56966428, compoundYield 47.9%

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 the 2-fluoro-benzenesulfonyl chloride (92 mg, 0.63 mmol) was 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]-2-fluoro-benzenesulfonamide (113 mg, yield: 44%) 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-e1c1149359ca40c8b0b5da13c2072f67
Source dataset
uspto-grants-2013_10
Patent number
US08546427B2

Reaction notes

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