1-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole → 5-[6-(1-Methyl-1h-pyrazol-5-yl)pyridin-3-yl]-2-nitrothiophene-3-carboxamide

HRID 385739Notes

Reaction equation

HRID 385739 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([C:8]2[S:12][C:11]([N+:13]([O-:15])=[O:14])=[C:10]([C:16]([NH2:18])=[O:17])[CH:9]=2)=[CH:4][CH:3]=1.[CH3:19][N:20]1[C:24](B2OC(C)(C)C(C)(C)O2)=[CH:23][CH:22]=[N:21]1>O1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:19][N:20]1[C:24]([C:2]2[N:7]=[CH:6][C:5]([C:8]3[S:12][C:11]([N+:13]([O-:15])=[O:14])=[C:10]([C:16]([NH2:18])=[O:17])[CH:9]=3)=[CH:4][CH:3]=2)=[CH:23][CH:22]=[N:21]1

Participants

5

Reactant 2

HCID 49129081-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 595256485-(6-Chloropyridin-3-yl)-2-nitrothiophene-3-carboxamide

Product 1

HCID 595256265-[6-(1-Methyl-1h-pyrazol-5-yl)pyridin-3-yl]-2-nitrothiophene-3-carboxamide

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
150 °C

Procedure

5-(6-Chloropyridin-3-yl)-2-nitrothiophene-3-carboxamide (300 mg, 1.06 mmol), 1-methyl-1H-pyrazole-5-boronic acid pinacol ester (352 mg, 1.69 mmol), and tetrakis(triphenylphosphine)palladium(0) (61.1 mg, 0.05 mmol) were dissolved in tetrahydrofuran (8.5 ml) and 2 M sodium carbonate (2.1 ml) and the mixture was bubbled with nitrogen for 5 min. The reaction was then heated in the microwave to 150° C. for 15 min. The mixture was poured into ethyl acetate and water and extracted with ethyl acetate (3×100 mL). The combined organic fractions were washed with brine, dried over magnesium sulfate, filtered and the solvent was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/hexane to yield the title compound as a yellow solid.

Workup

  1. custom2 M sodium carbonate (2.1 ml) and the mixture was bubbled with nitrogen for 5 min
  2. additionThe mixture was poured into ethyl acetate and water
  3. extractionextracted with ethyl acetate (3×100 mL)
  4. washThe combined organic fractions were washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel
  9. washeluting with ethyl acetate/hexane

Sources & evidence

ORD record
ord-d4f603f1deda4e8c8d109b975946028e
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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