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

HRID 573648Notes

Reaction equation

HRID 573648 reaction equation
[Br:1][C:2]1[S:12][C:5]2[N:6]=[C:7]([CH3:11])[CH:8]=[C:9]([NH2:10])[C:4]=2[C:3]=1[CH3:13].[Cl:14][C:15]1[CH:16]=[C:17]([S:21](Cl)(=[O:23])=[O:22])[CH:18]=[CH:19][CH:20]=1.CC(C)([O-])C.[Na+]>C1COCC1>[Br:1][C:2]1[S:12][C:5]2=[N:6][C:7]([CH3:11])=[CH:8][C:9]([NH:10][S:21]([C:17]3[CH:18]=[CH:19][CH:20]=[C:15]([Cl:14])[CH:16]=3)(=[O:23])=[O:22])=[C:4]2[C:3]=1[CH3:13]

Participants

5

Reactant 3

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 23676156Sodium t-butoxideHCID 68323880HCID 68323880, compound

Product 1

HCID 68324042N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamideYield 16.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-amine (Description 62) (1.351 g, 5.25 mmol) in THF (10 mL) was added 3-chlorobenzenesulfonyl chloride (1.11 mL, 7.88 mmol), sodium tert-butoxide (1.262 g, 13.13 mmol) and the mixture stirred at RT for 16 h. The mixture was then evaporated to dryness and the resulting material taken-up in water (10 mL) and extracted with ethyl acetate (20 mL×3). The organics were then combined, dried (phase separation cartridge) and concentrated. Purification on silica, eluting with a gradient of 0-20% ethyl acetate in cyclohexane, followed by MDAP (acidic conditions), afforded the title compound (380 mg). LCMS (A) m/z: 431/433 [M+1]+, Rt 1.22 min (acidic).

Workup

  1. customThe mixture was then evaporated to dryness
  2. extractionthe resulting material taken-up in water (10 mL) and extracted with ethyl acetate (20 mL×3)
  3. customdried
  4. custom(phase separation cartridge)
  5. concentrationconcentrated
  6. customPurification on silica
  7. washeluting with a gradient of 0-20% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-2406ee0552a74373ad6cd5febf0979dd
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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