Cesium fluoride → HCID 89876220, compound

HRID 2169765Notes

Reaction equation

HRID 2169765 reaction equation
Br[C:2]1[C:3]([O:21][CH3:22])=[C:4]([N:10]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([Cl:19])=[C:11]2[Cl:20])[C:5](=[O:9])[N:6]([CH3:8])[N:7]=1.[F-].[Cs+].[C:25](B1OC(C)(C)C(C)(C)O1)([CH3:27])=[CH2:26]>COCCOC.CCOC(C)=O>[Cl:20][C:11]1[N:10]([C:4]2[C:5](=[O:9])[N:6]([CH3:8])[N:7]=[C:2]([C:25]([CH3:27])=[CH2:26])[C:3]=2[O:21][CH3:22])[C:18]2[C:13]([C:12]=1[Cl:19])=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 109974264,4,5,5-Tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolaneHCID 89876340HCID 89876340, compound

Product 1

HCID 89876220HCID 89876220, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
150 °C

Procedure

6-bromo-4-(2,3-dichloroindol-1-yl)-5-methoxy-2-methyl-pyridazin-3-one (0.600 g, 1.49 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride dichloromethane complex (0.0608 g, 0.0744 mmol) and cesium fluoride (0.476 g, 2.98 mmol) are suspending in DME (3 mL) and 2-isopropenyl-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (330 μL, 1.79 mmol) is added. The resulting reaction mixture is heated under microwave irradiation to 150° C. for 20 min. The resulting reaction mixture is diluted with EtOAc (50 mL) and then washed with brine (50 mL). The organic layer was dried (MgSO4) and then concentrated under reduced pressure onto silica. Purification by flash chromatography (combiflash, 0 to 20% EtOAc/isohexane) afforded the desired product 4-(2,3-dichloroindol-1-yl)-6-isopropenyl-5-methoxy-2-methyl-pyridazin-3-one (503 mg, 1.38 mmol, 93%) as a pale brown oil.

Workup

  1. customThe resulting reaction mixture
  2. customThe resulting reaction mixture
  3. washwashed with brine (50 mL)
  4. dry with materialThe organic layer was dried (MgSO4)
  5. concentrationconcentrated under reduced pressure onto silica
  6. customPurification by flash chromatography (combiflash, 0 to 20% EtOAc/isohexane)

Sources & evidence

ORD record
ord-6f2fce52763e46df95ce05210738b34d
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

Loading…