Ammonium formate → HCID 67158102, compound

HRID 548807Notes

Reaction equation

HRID 548807 reaction equation
C([O-])=O.[NH4+].Br[C:6]1[N:7]=[N:8][C:9]([O:12][CH2:13][C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[CH:10][CH:11]=1>C(O)C.[Pd]>[CH3:19][C:18]1[O:17][N:16]=[C:15]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[C:14]=1[CH2:13][O:12][C:9]1[N:8]=[N:7][CH:6]=[CH:11][CH:10]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formate2×HCID 426296533-Bromo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine

Product 1

HCID 67158102HCID 67158102, compoundYield 38%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

Ammonium formate (0.20 g, 3.2 mmol) was added to a solution of 3-bromo-6-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridazine (0.54 g, 1.6 mmol) in ethanol (8 mL). The reaction flask was flushed with argon. Palladium on charcoal (10%, 0.05 g) was added and the mixture was heated to 40° C. After 16 h, additional ammonium formate (0.20 g, 3.2 mmol) and palladium on charcoal (10%, 0.05 g) was added and the mixture was heated to 40° C. for another 24 h. The mixture was filtered, concentrated and extracted (ethyl acetate/sodium bicarbonate solution). The organic layer was dried over sodium sulfate, concentrated and chromatographed (SiO2, heptane:ethyl acetate=100:0 to 60:40) to afford the title compound (160 mg, 38%) as a colorless oil. MS: m/e=268.1 [M+H]+.

Workup

  1. customThe reaction flask was flushed with argon
  2. additionPalladium on charcoal (10%, 0.05 g) was added
  3. temperaturethe mixture was heated to 40° C. for another 24 h
  4. filtrationThe mixture was filtered
  5. concentrationconcentrated
  6. extractionextracted (ethyl acetate/sodium bicarbonate solution)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. concentrationconcentrated
  9. customchromatographed (SiO2, heptane:ethyl acetate=100:0 to 60:40)

Sources & evidence

ORD record
ord-bc31749d90654f16b46a5269ce39a95c
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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