Ethanol → 6-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl ester

HRID 402404Notes

Reaction equation

HRID 402404 reaction equation
Cl[C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[N:11]([CH3:21])[N:12]=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:6][CH:7]=1.[C:22](=[O:25])([O-])[O-:23].[Na+].[Na+].[CH2:28](O)[CH3:29]>C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:28]([O:23][C:22]([C:2]1[N:3]=[N:4][C:5]([O:8][CH2:9][C:10]2[N:11]([CH3:21])[N:12]=[N:13][C:14]=2[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][N:16]=2)=[CH:6][CH:7]=1)=[O:25])[CH3:29]

Participants

6

Reactant 3

HCID 702EthanolHCID 10340Sodium CarbonateHCID 573350973-Chloro-6-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine

Product 1

HCID 573350986-(3-Methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine-3-carboxylic acid ethyl esterYield 84%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 635956Ferrocene-1,1'-bis-(diphenylphosphine)Catalyst

Conditions

Temperature
50 °C

Procedure

To a suspension of 3-chloro-6-(3-methyl-5-pyridin-2-yl-3H-[1,2,3]triazol-4-ylmethoxy)-pyridazine (620 mg, 2.05 mmol) in ethanol (10 mL) was added sodium carbonate (220 mg, 2.05 mmol) followed by 1,1′-bis(diphenylphosphino) ferrocene (115 mg, 0.21 mmol) and palladium(II) acetate (46 mg, 0.21 mmol). The reaction flask was filled with Ar three times after a short evacuation. The fourth time the flask was flushed with CO-gas (balloon). The mixture was stirred under CO atmosphere at 50° C. over night, then cooled to room temperature and filtered over dicalite and washed well with DCM. The filtrate was then evaporated. Purification by chromatography (silica, 0 to 50% ethyl acetate in heptane) afforded the title compound (582 mg, 84%) as an off white solid. MS: m/e=341.1 [M+H]+.

Workup

  1. additionThe reaction flask was filled with Ar three times after a short evacuation
  2. customThe fourth time the flask was flushed with CO-gas (balloon)
  3. temperaturecooled to room temperature
  4. filtrationfiltered over dicalite
  5. washwashed well with DCM
  6. customThe filtrate was then evaporated
  7. customPurification by chromatography (silica, 0 to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-a3a897fbbe854111895402b4d11a7548
Source dataset
uspto-grants-2014_06
Patent number
US08742097B2

Reaction notes

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