Toluene → HCID 57910772, compound

HRID 1644879Notes

Reaction equation

HRID 1644879 reaction equation
[CH3:1][C:2]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[N:28]=[N:29][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:31][CH:32]=2)=[CH:23][CH:22]=1)([C:6]1[CH:11]=[CH:10][C:9](B2OC(C)(C)C(C)(C)O2)=[CH:8][N:7]=1)[CH:3]([CH3:5])[CH3:4].Br[C:38]1[CH:39]=[N:40][CH:41]=[C:42]([O:44][CH3:45])[CH:43]=1.C(=O)([O-])[O-].[Na+].[Na+].C1(C)C=CC=CC=1>CCO.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:1][C:2]([C:6]1[N:7]=[CH:8][C:9]([C:38]2[CH:39]=[N:40][CH:41]=[C:42]([O:44][CH3:45])[CH:43]=2)=[CH:10][CH:11]=1)([C:21]1[CH:22]=[CH:23][C:24]([C:27]2[N:28]=[N:29][C:30]([C:33]([F:34])([F:35])[F:36])=[CH:31][CH:32]=2)=[CH:25][CH:26]=1)[CH:3]([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 1140TolueneHCID 10340Sodium CarbonateHCID 8171633-Bromo-5-methoxypyridineHCID 57910778HCID 57910778, compound

Product 1

HCID 57910772HCID 57910772, compound

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 702EthanolSolvent

Conditions

Temperature
95 °C

Procedure

[1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (14.0 mg, 0.0190 mmol) was added to a stirred solution of 8d (47.0 mg, 0.0950 mmol), 3-bromo-5-methoxypyridine (23.0 mg, 4.43 mmol) and sodium carbonate (100 μL of a 2.0 M aqueous solution, 0.200 mmol) in EtOH:toluene (500 μL of an 80:20 mixture, respectively) at rt. The resulting solution was heated to 95° C. for approximately 5 h. After cooling to rt, the reaction mixture was filtered through a short column of CELITE®, eluting with EtOAc. The filtrate was washed with water, brine, dried (sodium sulfate) and concentrated in vacuo. The crude residue was purified by flash chromatography on silica gel (gradient elution; 20%-50% EtOAc/hexanes as eluent) to furnish the title compound 8e. m/z (ES) 479 (MH)+.

Workup

  1. customat rt
  2. temperatureAfter cooling to rt
  3. filtrationthe reaction mixture was filtered through a short column of CELITE®
  4. washeluting with EtOAc
  5. washThe filtrate was washed with water, brine
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chromatography on silica gel (gradient elution; 20%-50% EtOAc/hexanes as eluent)

Sources & evidence

ORD record
ord-849ff0bb7f0e449d8b07122122f8fe49
Source dataset
uspto-grants-2012_02
Patent number
US08124628B2

Reaction notes

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