Potassium Carbonate → HCID 68324153, compound

HRID 573654Notes

Reaction equation

HRID 573654 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].CC1(C)C(C)(C)OB([C:32]2[CH:33]=[N:34][O:35][CH:36]=2)O1.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:32]4[CH:33]=[N:34][O:35][CH:36]=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 164141804-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2-oxazoleHCID 68324042N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamide

Product 1

HCID 68324153HCID 68324153, compoundYield 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) (80 mg, 0.185 mmol) in 1,4-dioxane (2 mL) and water (1 mL) was added 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole (36.1 mg, 0.185 mmol), bis(triphenylphosphine)palladium(II) chloride (13.01 mg, 0.019 mmol), and potassium carbonate (90 mg, 0.649 mmol) and the reaction mixture heated at 100° C. using a microwave reactor for 1.5 h. The reaction mixture was then filtered through celite, washing with DCM (30 mL) and the filtrate evaporated to dryness. The resulting material was then purified by MDAP (acidic conditions), to afford the title compound (4.67 mg). LCMS (A) m/z: 420 [M+1]+, Rt 1.09 min (acidic).

Workup

  1. customfor 1.5 h
  2. filtrationThe reaction mixture was then filtered through celite
  3. washwashing with DCM (30 mL)
  4. customthe filtrate evaporated to dryness
  5. customThe resulting material was then purified by MDAP (acidic conditions)

Sources & evidence

ORD record
ord-295ab573ff9b40018cde36ee0d1f38ee
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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