Cesium carbonate → HCID 71767899, compound

HRID 1477694Notes

Reaction equation

HRID 1477694 reaction equation
[N:1]1([C:7]2[N:12]=[CH:11][N:10]([CH2:13][N:14]3[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[N:15]3)[C:9](=[O:23])[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([O:31][CH3:32])[CH:26]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C(OCC)(=O)C.O.O1CCOCC1>[CH3:32][O:31][C:27]1[CH:26]=[C:25]([N:4]2[CH2:5][CH2:6][N:1]([C:7]3[N:12]=[CH:11][N:10]([CH2:13][N:14]4[CH:18]=[CH:17][C:16]([C:19]([F:20])([F:21])[F:22])=[N:15]4)[C:9](=[O:23])[N:8]=3)[CH2:2][CH2:3]2)[CH:30]=[CH:29][CH:28]=1

Participants

9

Reactant 4

HCID 10796Cesium carbonateHCID 169713-BromoanisoleHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 117849087HCID 117849087, compound

Product 1

HCID 71767899HCID 71767899, compoundYield 32%

Reagents, catalysts & solvents 4

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

A 1,4-dioxane solution (1.0 mL) of 4-(piperazin-1-yl)-1-{[3-(trifluoromethyl)-1H-pyrazol-1-yl]methyl}-1,3,5-triazin-2(1H)-one (50 mg, 0.07 mmol) synthesized in Reference Synthesis Example 17, 1-bromo-3-methoxybenzene (8.6 μL, 0.07 mmol), tris(dibenzylideneacetone)dipalladium (0) (6.2 mg, 0.007 mmol), dicyclohexyl(2′,4′,6′-triisopropyl-[1,1′-biphenyl]-2-yl)phosphine (6.5 mg, 0.01 mmol), and cesium carbonate (44 mg, 0.14 mmol) was stirred in a nitrogen atmosphere at 80° C. for 1 day. After the completion of the reaction, water was added to the reaction solution and extraction with ethyl acetate from the resultant reaction solution was performed three times. The organic layer was washed with brine, was dried over anhydrous sodium sulfate, and was concentrated under reduced pressure. The resultant residue was purified by preparative thin-layer chromatography (hexane/ethyl acetate=1/1 (v/v)) to obtain the title compound (9.4 mg, yield: 32%).

Workup

  1. customreaction solution
  2. washThe organic layer was washed with brine
  3. dry with materialwas dried over anhydrous sodium sulfate
  4. concentrationwas concentrated under reduced pressure
  5. customThe resultant residue was purified by preparative thin-layer chromatography (hexane/ethyl acetate=1/1 (v/v))

Sources & evidence

ORD record
ord-ba6d95e2acbb4908ab5b3d09f606fdfd
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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