Ammonium formate → HCID 46893583, compound

HRID 2381081Notes

Reaction equation

HRID 2381081 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10]2[CH2:15][CH2:14][N:13]([C:16]3[CH2:17][CH2:18][C:19]4[N:20]([C:22]([C:25]([F:28])([F:27])[F:26])=[N:23][N:24]=4)[N:21]=3)[CH2:12][CH:11]=2)=[CH:2]1.C([O-])=O.[NH4+]>[Pd].C(O)C>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH:10]2[CH2:11][CH2:12][N:13]([C:16]3[CH2:17][CH2:18][C:19]4[N:20]([C:22]([C:25]([F:28])([F:27])[F:26])=[N:23][N:24]=4)[N:21]=3)[CH2:14][CH2:15]2)=[CH:2]1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 46893454HCID 46893454, compound

Product 1

HCID 46893583HCID 46893583, compoundYield 69%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
78 °C

Procedure

10% Palladium on carbon (23.96 mg, 0.02 mmol) was added to 6-[4-(1H-indol-3-yl)-5,6-dihydropyridin-1(2H)-yl]-3-(trifluoromethyl)-7,8-dihydro-[1,2,4]triazolo[4,3-b]pyridazine (obtained as described in Example 2) (87 mg, 0.23 mmol) and ammonium formate (71.0 mg, 1.13 mmol) in ethanol (20 mL). The resulting mixture was stirred at 78° C. for 2 hours. The reaction mixture was cooled to room temperature, evaporated to dryness, then re-dissolved in ethyl acetate (25 mL) and the solution washed sequentially with water (20 mL) and saturated brine (10 mL). The organic layer was dried over MgSO4, filtered and evaporated to afford 6-[4-(1H-indol-3-yl)piperidin-1-yl]-3-(trifluoromethyl)-7,8-dihydro[1,2,4]triazolo[4,3-b]pyridazine (60.0 mg, 69%) as a solid.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customevaporated to dryness
  3. dissolutionre-dissolved in ethyl acetate (25 mL)
  4. washthe solution washed sequentially with water (20 mL) and saturated brine (10 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-47668a127f98490e993dcf1070082919
Source dataset
uspto-grants-2012_09
Patent number
US08258140B2

Reaction notes

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