Sodium Carbonate → 7-Ethyl-4-(4-fluorophenyl)-7H-imidazo[4,5-c]pyridazine

HRID 1846002Notes

Reaction equation

HRID 1846002 reaction equation
Cl[C:2]1[C:3]2[N:10]=[CH:9][N:8]([CH2:11][CH3:12])[C:4]=2[N:5]=[N:6][CH:7]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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>[CH2:11]([N:8]1[C:4]2[N:5]=[N:6][CH:7]=[C:2]([C:17]3[CH:18]=[CH:19][C:14]([F:13])=[CH:15][CH:16]=3)[C:3]=2[N:10]=[CH:9]1)[CH3:12]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 552967654-chloro-7-ethyl-7H-imidazo(4,5-c)pyridazine

Product 1

HCID 867232317-Ethyl-4-(4-fluorophenyl)-7H-imidazo[4,5-c]pyridazineYield 55%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a room temperature solution of 4-chloro-7-ethyl-7H-imidazo[4,5-c]pyridazine (Preparation 8, 9.6 g, 52.4 mmol) in dioxane (300 mL) was added 4-fluorobenzene boronic acid (8.8 g, 63 mmol) and an aqueous solution of Na2CO3 (1M, 260 mL, 262 mmol). The reaction mixture was degassed and purged with nitrogen gas 3 times. Tetrakis(triphenylphosphine)palladium(0) (1.2 g, 1.0 mmol) was then added and the mixture was heated to reflux for 4 hours. The organic solvent was removed in vacuo and the resulting aqueous mixture filtered. The filter cake was dried under vacuum to afford the title compound as a yellow solid in 55% yield, 7 g.

Workup

  1. customThe reaction mixture was degassed
  2. custompurged with nitrogen gas 3 times
  3. temperaturethe mixture was heated
  4. temperatureto reflux for 4 hours
  5. customThe organic solvent was removed in vacuo
  6. filtrationthe resulting aqueous mixture filtered
  7. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-96a4e5224f8f4056a293796670b78022
Source dataset
uspto-grants-2015_02
Patent number
US08952008B2

Reaction notes

Loading…