Benzenesulfonyl chloride → N-(3-(6-(4-methoxyphenyl)-9H-pyrido[2,3-b]indol-3-yl)phenyl)benzenesulfonamide

HRID 341301Notes

Reaction equation

HRID 341301 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]2[N:18]=[CH:19][C:20]([C:22]4[CH:23]=[C:24]([NH2:28])[CH:25]=[CH:26][CH:27]=4)=[CH:21][C:12]3=2)=[CH:5][CH:4]=1.[C:29]1([S:35](Cl)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[NH:14][C:13]2[N:18]=[CH:19][C:20]([C:22]4[CH:23]=[C:24]([NH:28][S:35]([C:29]5[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=5)(=[O:37])=[O:36])[CH:25]=[CH:26][CH:27]=4)=[CH:21][C:12]3=2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 461841583-(6-(4-methoxyphenyl)-9H-pyrido[2,3-b]indol-3-yl)benzenamine

Product 1

HCID 46184159N-(3-(6-(4-methoxyphenyl)-9H-pyrido[2,3-b]indol-3-yl)phenyl)benzenesulfonamideYield 50%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 3-(6-(4-methoxyphenyl)-9H-pyrido[2,3-b]indol-3-yl)benzenamine (23 mg, 0.06 mmol, 1 equiv.), in anhydrous pyridine (0.300 ml), benzenesulfonyl chloride (0.009 ml) is added under argon. The reaction is carried out at room temperature for 3 hours and is then quenched with H2O (5 ml). The aqueous layer is extracted with AcOEt (3×5 ml) and CH2Cl2 (5 ml). The organic layers are dried over MgSO4 and concentrated under reduced pressure. The crude product is purified over silica gel chromatography (eluant CH2Cl2/AcOEt 7:3) to afford the product as a white solid (15 mg, 0.03 mmol) in 50% yield.

Workup

  1. customis then quenched with H2O (5 ml)
  2. extractionThe aqueous layer is extracted with AcOEt (3×5 ml) and CH2Cl2 (5 ml)
  3. dry with materialThe organic layers are dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product is purified over silica gel chromatography (eluant CH2Cl2/AcOEt 7:3)

Sources & evidence

ORD record
ord-b6f275b5a3d548419554447f2b272292
Source dataset
uspto-grants-2014_11
Patent number
US08895744B2

Reaction notes

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