Potassium Carbonate → HCID 178428782, compound

HRID 573652Notes

Reaction equation

HRID 573652 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].[NH:24]1[CH:28]=[CH:27][C:26](B(O)O)=[N: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:28]4[CH:27]=[CH:26][NH:25][N:24]=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 68324042N-(2-bromo-3,6-dimethylthieno[2,3-b]pyridin-4-yl)-3-chlorobenzenesulfonamideHCID 178514837HCID 178514837, compound

Product 1

HCID 178428782HCID 178428782, compoundYield 10.4%

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), 1H-pyrazol-3-ylboronic acid (20.73 mg, 0.185 mmol) and bis(triphenylphosphine)palladium(II) chloride (13.01 mg, 0.019 mmol) in 1,4-dioxane (2 mL) and water (1 mL) was added potassium carbonate (90 mg, 0.649 mmol) and the mixture heated to 100° C. using a microwave reactor for 30 min. The mixture was then evaporated to dryness and purified by MDAP (acidic conditions), followed by MDAP (basic conditions), to afford the title compound (8.07 mg). LCMS (A) m/z: 417 [M−1]−, Rt 0.99 min (acidic).

Workup

  1. customfor 30 min
  2. customThe mixture was then evaporated to dryness
  3. custompurified by MDAP (acidic conditions)

Sources & evidence

ORD record
ord-8450e618316349beacd47987f3a57ca5
Source dataset
uspto-grants-2015_05
Patent number
US09029545B2

Reaction notes

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