Sodium Carbonate → HCID 15950606, compound

HRID 1360668Notes

Reaction equation

HRID 1360668 reaction equation
Cl[C:2]1[N:3]2[C:8]([CH:9]=[CH:10][CH:11]=1)=[C:7]([C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:19])[C:6](=[O:20])[CH:5]=[CH:4]2.[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1B(O)O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[C:2]1[N:3]2[C:8]([CH:9]=[CH:10][CH:11]=1)=[C:7]([C:12]1[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:19])[C:6](=[O:20])[CH:5]=[CH:4]2

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343222-Chlorophenylboronic acidHCID 57700381HCID 57700381, compound

Product 1

HCID 15950606HCID 15950606, compoundYield 42%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-chloro-1-(2,6-dichlorophenyl)-2H-quinolizin-2-one (Example 1, 54 mg) in DME was added 2-chlorophenylboronic acid (31 mg), palladium acetate (3.5 mg), triphenylphosphine (8 mg) and 2N sodium carbonate (0.32 mL). The mixture was heated to 80° C. for 12 hrs, then cooled to room temperature, and diluted with ethyl acetate/saturated aqueous sodium bicarbonate. The organic layers were dried over magnesium sulfate and concentrated. The residue was purified by silica gel (methylene chloride/acetone=2/1) and recrystallized from methylene chloride/acetone/hexanes to give title compound as a yellowish solid (28 mg).

Workup

  1. temperaturecooled to room temperature
  2. dry with materialThe organic layers were dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel (methylene chloride/acetone=2/1)
  5. customrecrystallized from methylene chloride/acetone/hexanes

Sources & evidence

ORD record
ord-5f86e7792cf04cbda57c8bd2389518b1
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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