Potassium Carbonate → HCID 53250695, compound

HRID 573649Notes

Reaction equation

HRID 573649 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].[CH3:24][O:25][C:26]1[CH:27]=[C:28](B(O)O)[CH:29]=[CH:30][CH:31]=1.C(=O)([O-])[O-].[K+].[K+]>O.O1CCOCC1.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:30]4[CH:29]=[CH:28][CH:27]=[C:26]([O:25][CH3:24])[CH:31]=4)=[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 2734370(3-Methoxyphenyl)boronic acidHCID 68324042N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide

Product 1

HCID 53250695HCID 53250695, compoundYield 34.6%

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) (100 mg, 0.232 mmol) in water (1 mL) and 1,4-dioxane (2 mL) was added [3-(methyloxy)phenyl]boronic acid (52.8 mg, 0.347 mmol), bis(triphenylphosphine)palladium(II) chloride (16.26 mg, 0.023 mmol), potassium carbonate (96 mg, 0.695 mmol) and the mixture heated to 100° C. for 15 min using a microwave reactor. The mixture was then filtered through celite, washing with ethyl acetate (30 mL) and DCM (20 mL). The organics were then combined, dried (phase separation cartridge) and concentrated. The residue was then purified by MDAP (basic conditions), to afford the title compound (36.8 mg). LCMS (A) m/z: 459 [M+1]+, Rt 1.32 min (acidic).

Workup

  1. filtrationThe mixture was then filtered through celite
  2. washwashing with ethyl acetate (30 mL) and DCM (20 mL)
  3. customdried
  4. custom(phase separation cartridge)
  5. concentrationconcentrated
  6. customThe residue was then purified by MDAP (basic conditions)

Sources & evidence

ORD record
ord-e5bbe5c59cab4c5498e39ae5ccaad895
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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