Potassium Carbonate → 3-Chloro-N-[3,6-dimethyl-2-(3-quinolinyl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamide

HRID 573651Notes

Reaction equation

HRID 573651 reaction equation
Br[C:2]1[S:22][C:5]2=[N:6][C:7]([CH3:21])=[CH:8][C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[CH3:23].[N:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26](B(O)O)[CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:20][C:16]1[CH:15]=[C:14]([S:11]([NH:10][C:9]2[CH:8]=[C:7]([CH3:21])[N:6]=[C:5]3[S:22][C:2]([C:26]4[CH:25]=[N:24][C:33]5[C:28]([CH:27]=4)=[CH:29][CH:30]=[CH:31][CH:32]=5)=[C:3]([CH3:23])[C:4]=23)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2734663Quinoline-3-boronic acidHCID 68324042N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide

Product 1

HCID 683239103-Chloro-N-[3,6-dimethyl-2-(3-quinolinyl)thieno[2,3-b]pyridin-4-yl]benzenesulfonamideYield 31.7%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide (Example 77) (90 mg, 0.208 mmol) in 1,4-dioxane (2 mL) and water (1 mL) was added 3-quinolinylboronic acid (72.1 mg, 0.417 mmol), bis(triphenylphosphine)palladium(II) chloride (14.63 mg, 0.021 mmol) and potassium carbonate (101 mg, 0.730 mmol) and the reaction mixture heated at 100° C. for 30 min using a microwave reactor. The mixture was then filtered through celite, washing with DCM (30 mL×2) and the filtrate dried (phase separation cartridge) and concentrated. This residue was then purified by MDAP (basic conditions) and then further triturated with MeOH (2 mL) and dried, to afford the title compound (31.61 mg). LCMS (A) m/z: 480 [M+1]+, Rt 1.23 min (acidic).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washwashing with DCM (30 mL×2)
  3. customthe filtrate dried
  4. custom(phase separation cartridge)
  5. concentrationconcentrated
  6. customThis residue was then purified by MDAP (basic conditions)
  7. customfurther triturated with MeOH (2 mL)
  8. customdried

Sources & evidence

ORD record
ord-c128f1f348a840b4a9a30a55766482d3
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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