3-Chlorobenzenesulphonyl chloride → 3-chloro-N-[3-(3-chlorophenyl)-2,6-dimethylthieno[2,3-b]pyridin-4-yl]benzenesulfonamide

HRID 573612Notes

Reaction equation

HRID 573612 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:15]([NH2:17])=[CH:14][C:13]([CH3:18])=[N:12][C:11]=3[S:10][C:9]=2[CH3:19])[CH:5]=[CH:6][CH:7]=1.CC(C)([O-])C.[K+].[Cl:26][C:27]1[CH:28]=[C:29]([S:33](Cl)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1>C1COCC1>[Cl:26][C:27]1[CH:28]=[C:29]([S:33]([NH:17][C:15]2[CH:14]=[C:13]([CH3:18])[N:12]=[C:11]3[S:10][C:9]([CH3:19])=[C:8]([C:4]4[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=4)[C:16]=23)(=[O:35])=[O:34])[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 23665647Potassium tert-butoxideHCID 683240173-(3-Chlorophenyl)-2,6-dimethylthieno[2,3-b]pyridin-4-amine

Product 1

HCID 683240713-chloro-N-[3-(3-chlorophenyl)-2,6-dimethylthieno[2,3-b]pyridin-4-yl]benzenesulfonamideYield 42.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(3-chlorophenyl)-2,6-dimethylthieno[2,3-b]pyridin-4-amine (100 mg, 0.346 mmol) (Description 9) in THF (3 mL) was added potassium tert-butoxide (155 mg, 1.385 mmol) and the mixture stirred for 5 min before the addition of 3-chlorobenzenesulfonyl chloride (0.049 mL, 0.346 mmol). The mixture was then stirred for 1 h and the solvent then removed in vacuo. Ethyl acetate (10 mL) was then added and the mixture washed with water (3×10 mL). The organic layer was dried over MgSO4, filtered and the solvent removed in vacuo. Purification by chromatography on silica gel, eluting with a gradient of 0-30% ethyl acetate in cyclohexane, was followed by trituration with MeOH, to afford the title compound (67.8 mg). LCMS (A) m/z: 463 [M+1]+, Rt 1.09 min (basic), Rt 1.44 min (acidic).

Workup

  1. customthe solvent then removed in vacuo
  2. additionEthyl acetate (10 mL) was then added
  3. washthe mixture washed with water (3×10 mL)
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent removed in vacuo
  7. customPurification by chromatography on silica gel
  8. washeluting with a gradient of 0-30% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-d7ea2636a4fc4b819fbb9543cf358447
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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