Cesium carbonate → HCID 89876291, compound

HRID 2169763Notes

Reaction equation

HRID 2169763 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.[C:23](=O)([O-])[O-:24].[Cs+].[Cs+]>C1(C)C=CC=CC=1.CO.C(P(C(C)(C)C)C1C(OC)=CC=C(C)C=1C1C(C(C)C)=CC(C(C)C)=CC=1C(C)C)(C)(C)C>[Cl:20][C:11]1[N:10]([C:4]2[C:5](=[O:9])[N:6]([CH3:8])[N:7]=[C:2]([O:24][CH3:23])[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 2

HCID 10796Cesium carbonateHCID 89876340HCID 89876340, compound

Product 1

HCID 89876291HCID 89876291, compoundYield 66%

Reagents, catalysts & solvents 3

HCID 56641709(2',4'-Diisopropyl-3-methoxy-6-methyl-6'-propyl-2-biphenylyl)[bis(2-methyl-2-propanyl)]phosphineCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

6-bromo-4-(2,3-dichloroindol-1-yl)-5-methoxy-2-methyl-pyridazin-3-one (0.200 g, 0.496 mmol), Pd2Cl2(allyl)2 (2.7 mg, 0.00744 mmol), ditert-butyl-[6-methoxy-3-methyl-2-(2,4,6-triisopropylphenyl)phenyl]phosphane (11.6 mg, 0.0248 mmol) and dicesium carbonate (0.243 g, 0.744 mmol) are suspended in toluene (3 mL) and methanol (60 μL). The resulting reaction mixture is heated under microwave irradiation to 110° C. for 20 min. The resulting reaction mixture is filtered, washing with EtOAc and concentrated under reduced pressure onto silica. Purification by flash chromatography (combiflash, 0 to 30% EtOAc/isohexane) afforded the desired product 4-(2,3-dichloroindol-1-yl)-5,6-dimethoxy-2-methyl-pyridazin-3-one (0.116 g, 0.3275 mmol, 66% yield) as a brown oil.

Workup

  1. customThe resulting reaction mixture
  2. customThe resulting reaction mixture
  3. filtrationis filtered
  4. washwashing with EtOAc
  5. concentrationconcentrated under reduced pressure onto silica
  6. customPurification by flash chromatography (combiflash, 0 to 30% EtOAc/isohexane)

Sources & evidence

ORD record
ord-454c3996c63c4682b517fac75647134e
Source dataset
uspto-grants-2015_06
Patent number
US09049864B2

Reaction notes

Loading…