Ethanol → HCID 16065180, compound

HRID 1360701Notes

Reaction equation

HRID 1360701 reaction equation
Br[C:2]1[CH:7]=[C:6]([F:8])[C:5]([C:9]2[C:10](=[O:26])[CH:11]=[CH:12][N:13]3[C:18]=2[CH:17]=[CH:16][CH:15]=[C:14]3[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=2)=[C:4]([F:27])[CH:3]=1.[N:28]1[CH:33]=[C:32](B(O)O)[CH:31]=[N:30][CH:29]=1.CCO.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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>[F:8][C:6]1[CH:7]=[C:2]([C:32]2[CH:33]=[N:28][CH:29]=[N:30][CH:31]=2)[CH:3]=[C:4]([F:27])[C:5]=1[C:9]1[C:10](=[O:26])[CH:11]=[CH:12][N:13]2[C:18]=1[CH:17]=[CH:16][CH:15]=[C:14]2[C:19]1[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 2795193(Pyrimidin-5-yl)boronic acidHCID 16065592HCID 16065592, compound

Product 1

HCID 16065180HCID 16065180, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 1-(4-bromo-2,6-difluorophenyl)-6-(4-fluorophenyl)-2H-quinolizin-2-one Example 44, 74 mg, 0.17 mmol) in toluene (5 mL) was added pyrimidin-5-ylboronic acid (42 mg, 0.34 mmol), tetrakis(triphenylphosphine)palladium (196 mg, 0.017 mmol), EtOH (0.5 mL) and 2N Na2CO3 (0.5 mL), and heated to 90° C. for 12 h. After cooling the reaction to room temperature, the mixture was concentrated. The crude residue was dissolved in EtOAc and washed with water, brine, dried over MgSO4, and concentrated. The crude material was purified using silica gel chromatography (CH2Cl2/EtOAc/MeOH) to give title compound.

Workup

  1. temperatureAfter cooling
  2. customthe reaction to room temperature
  3. concentrationthe mixture was concentrated
  4. dissolutionThe crude residue was dissolved in EtOAc
  5. washwashed with water, brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated
  8. customThe crude material was purified

Sources & evidence

ORD record
ord-ce97a422356b4595b61c1fb5ac37cf38
Source dataset
uspto-grants-2011_02
Patent number
US07879875B2

Reaction notes

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