3-Chlorobenzenesulphonyl chloride → N-(3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide

HRID 573633Notes

Reaction equation

HRID 573633 reaction equation
[Br:1][C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][C:7]([CH3:12])=[N:6][C:5]=2[S:4][C:3]=1[CH3:13].CC(C)([O-])C.[K+].[Cl:20][C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1>C1COCC1>[Br:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([CH3:12])=[CH:8][C:9]=2[NH:11][S:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([Cl:20])[CH:22]=2)(=[O:29])=[O:28])[S:4][C:3]=1[CH3:13]

Participants

5

Reactant 3

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 23665647Potassium tert-butoxideHCID 683238623-Bromo-2,6-dimethylthieno[2,3-b]pyridin-4-amine

Product 1

HCID 68324076N-(3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamideYield 48.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-bromo-2,6-dimethylthieno[2,3-b]pyridin-4-amine (1.6 g, 6.22 mmol) (Description 8) in THF (30 mL) was added potassium tert-butoxide (2.79 g, 24.89 mmol) and the mixture stirred for 5 min before adding 3-chlorobenzenesulfonyl chloride (2.190 mL, 15.56 mmol). The mixture was stirred for 1 h and the solvent was then removed in vacuo. Ethyl acetate (50 mL) was added and the mixture washed with water (3×30 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, afforded the title compound (1.3 g). LCMS (A) m/z: 431/433 [M+1]+, Rt 1.38 min (acidic).

Workup

  1. stirringThe mixture was stirred for 1 h
  2. customthe solvent was then removed in vacuo
  3. additionEthyl acetate (50 mL) was added
  4. washthe mixture washed with water (3×30 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customthe solvent removed in vacuo
  8. customPurification by chromatography on silica gel
  9. washeluting with a gradient of 0-30% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-6cd5a0b5c60144cc828e55469057288a
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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