3-Chlorobenzenesulphonyl chloride → N-{2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide

HRID 573615Notes

Reaction equation

HRID 573615 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[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1.CC(C)([O-])C.[Na+].[Cl:27][C:28]1[CH:29]=[C:30]([S:34](Cl)(=[O:36])=[O:35])[CH:31]=[CH:32][CH:33]=1.[Cl-].[NH4+]>C1COCC1>[Br:1][C:2]1[S:12][C:5]2=[N:6][C:7]([CH3:11])=[CH:8][C:9]([NH:10][S:34]([C:30]3[CH:31]=[CH:32][CH:33]=[C:28]([Cl:27])[CH:29]=3)(=[O:36])=[O:35])=[C:4]2[C:3]=1[C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([O:19][CH3:20])[CH:14]=1

Participants

6

Reactant 4

HCID 179093-Chlorobenzenesulphonyl chlorideHCID 25517Ammonium ChlorideHCID 23676156Sodium t-butoxideHCID 683240582-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine

Product 1

HCID 53250396N-{2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamideYield 49.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-amine (213 mg, 0.610 mmol) (Description 17) in THF (5 mL) was added sodium tert-butoxide (234 mg, 2.440 mmol) at RT and the mixture stirred for 15 min before the addition of 3-chlorobenzenesulfonyl chloride (0.172 mL, 1.220 mmol). The mixture was then stirred for 3.5 h. Saturated ammonium chloride solution (20 mL) was added to the mixture which was then extracted with ethyl acetate (2×15 mL). The combined organics were washed with brine (20 mL), dried and concentrated. Purification by chromatography on silica gel, eluting with a gradient of 0-30% ethyl acetate in cyclohexane, afforded the title compound (157 mg). LCMS (A) m/z: 523/525 [M+1]+, Rt 1.54 min (acidic), Rt 1.83 min (basic).

Workup

  1. extractionwas then extracted with ethyl acetate (2×15 mL)
  2. washThe combined organics were washed with brine (20 mL)
  3. customdried
  4. concentrationconcentrated
  5. customPurification by chromatography on silica gel
  6. washeluting with a gradient of 0-30% ethyl acetate in cyclohexane

Sources & evidence

ORD record
ord-d3c212fc01874a48bd6a330ef540f38b
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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