Benzenesulfonyl chloride → N-(1-Benzenesulfonyl-6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

HRID 1363121Notes

Reaction equation

HRID 1363121 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH2:7][CH:6]([NH:12][S:13]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)(=[O:15])=[O:14])[CH2:5]2.[C:22]1([S:28](Cl)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1>[C:22]1([S:28]([N:8]2[C:9]3[C:4](=[CH:3][C:2]([Br:1])=[CH:11][CH:10]=3)[CH2:5][CH:6]([NH:12][S:13]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)(=[O:14])=[O:15])[CH2:7]2)(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 18177113N-(6-Bromo-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamide

Product 1

HCID 59778145N-(1-Benzenesulfonyl-6-bromo-1,2,3,4-tetrahydroquinolin-3-yl)-benzenesulfonamideYield 93%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of compound 87A (98 mg, 0.299 mmol) in pyridine (3 ml) was added benzenesulfonyl chloride (0.042 mL, 0.33 mmol). The mixture was stirred at RT overnight, then concentrated. The residue was chromatographed (10 g silica gel) eluting with EtOAc (0-60%) in hexane to give the title compound (140 mg, 93%) as a white foam. HPLC: 99% at 7.06 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A 90% H2O−10% MeOH−0.1% H3PO4 and B=10% H2O−90% MeOH−0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 529 [M+Na]+.

Workup

  1. concentrationconcentrated
  2. customThe residue was chromatographed (10 g silica gel)
  3. washeluting with EtOAc (0-60%) in hexane

Sources & evidence

ORD record
ord-a717083e0f1b46dca0bfb5c1d2102b30
Source dataset
uspto-grants-2011_02
Patent number
US07884113B2

Reaction notes

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