Potassium Carbonate → HCID 68324147, compound

HRID 573650Notes

Reaction equation

HRID 573650 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].[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH:26]=[C:25]1B(O)O.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>[O:24]1[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=2[CH:26]=[C:25]1[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]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2776266Benzo[b]furan-2-boronic acidHCID 68324042N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide

Product 1

HCID 68324147HCID 68324147, compoundYield 10%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

To solution of N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide (Example 77) (100 mg, 0.232 mmol) in 1,4-dioxane (2 mL) and water (1 mL) was added 1-benzofuran-2-ylboronic acid (56.3 mg, 0.347 mmol), bis(triphenylphosphine)palladium(II) chloride (16.26 mg, 0.023 mmol) and potassium carbonate (112 mg, 0.811 mmol) and the reaction mixture heated at 100° C. using a microwave reactor for 30 min. The mixture was then filtered through celite, washing with DCM (20 mL×2) and the filtrate dried (phase separation cartridge) and concentrated. The residue was then purified by MDAP (acidic conditions), followed by MDAP (basic conditions) to afford the title compound (10.89 mg). LCMS (A) m/z: 469 [M+1]+, Rt 1.42 min (acidic).

Workup

  1. customfor 30 min
  2. filtrationThe mixture was then filtered through celite
  3. washwashing with DCM (20 mL×2)
  4. customthe filtrate dried
  5. custom(phase separation cartridge)
  6. concentrationconcentrated
  7. customThe residue was then purified by MDAP (acidic conditions)

Sources & evidence

ORD record
ord-7595443073714f268bc506bd37895347
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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