4-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholine → 5-(6-Morpholin-4-ylpyridin-3-yl)-2-nitrothiophene-3-carboxamide

HRID 1967149Notes

Reaction equation

HRID 1967149 reaction equation
Br[C:2]1[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:12])=[O:11])[CH:3]=1.CC1(C)C(C)(C)OB([C:21]2[CH:22]=[CH:23][C:24]([N:27]3[CH2:32][CH2:31][O:30][CH2:29][CH2:28]3)=[N:25][CH:26]=2)O1>C1COCC1.C(OCC)(=O)C.O>[N:27]1([C:24]2[N:25]=[CH:26][C:21]([C:2]3[S:6][C:5]([N+:7]([O-:9])=[O:8])=[C:4]([C:10]([NH2:12])=[O:11])[CH:3]=3)=[CH:22][CH:23]=2)[CH2:28][CH2:29][O:30][CH2:31][CH2:32]1

Participants

6

Reactant 2

HCID 27953634-(5-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-2-pyridinyl)morpholineHCID 534029485-Bromo-2-nitrothiophene-3-carboxamide

Product 1

HCID 595257935-(6-Morpholin-4-ylpyridin-3-yl)-2-nitrothiophene-3-carboxamide

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-2-nitrothiophene-3-carboxamide (2.50 g, 9.96 mmol) and 4-[5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine-2-yl]morpholine (2.89 g, 9.96 mmol) were combined in THF (40 ml). Tetrakis(triphenylphoshine)palladium(0) (0.58 g, 0.50 mmol) was added and the reaction mixture was heated to reflux overnight. After cooling to room temperature, the mixture was diluted with ethyl acetate (500 ml) and water (500 ml). A red solid crashed out. The mixture was filtered and the solid was washed with ethyl acetate to yield the title compound as a red solid.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux overnight
  3. filtrationThe mixture was filtered
  4. washthe solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-a1f9ba6884274c8990e746982d0d957d
Source dataset
uspto-grants-2013_04
Patent number
US08420695B2

Reaction notes

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