Cesium carbonate → HCID 73319789, compound

HRID 2063622Notes

Reaction equation

HRID 2063622 reaction equation
C(C1C(N)=CC=CC=1B(O)O)(OC(C)(C)C)=O.[Cl-].CC1C=C(C)C=C(C)C=1[N+]1C=CN(C2C(C)=CC(C)=CC=2C)C=1.C(=O)([O-])[O-].[Cs+].[Cs+].C(OC(=O)[NH:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[C:61]1[CH:66]=[C:65]([NH:67][N:68]=[C:69]([C:71]2[CH:76]=[CH:75][C:74]([CH3:77])=[CH:73][CH:72]=2)[CH3:70])[N:64]=[C:63]([CH3:78])[N:62]=1)(C)(C)C>O1CCOCC1.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]>[CH3:78][C:63]1[N:62]=[C:61]([C:56]2[CH:57]=[CH:58][CH:59]=[CH:60][C:55]=2[NH2:54])[CH:66]=[C:65]([NH:67][N:68]=[C:69]([C:71]2[CH:72]=[CH:73][C:74]([CH3:77])=[CH:75][CH:76]=2)[CH3:70])[N:64]=1

Participants

7

Reactant 4

HCID 10796Cesium carbonateHCID 27342111,3-Bis(2,4,6-trimethylphenyl)imidazolium chlorideHCID 69126343HCID 69126343, compoundHCID 87711498HCID 87711498, compound

Product 1

HCID 73319789HCID 73319789, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Procedure

The title compound was prepared from (1)-1-(4-methylphenyl)ethanone (6-chloro-2-methylpyrimidin-4-yl)hydrazone (130 mg, 0.47 mmol), (2-BOC-aminophenyl)boronic acid (560 mg, 2.37 mmol), 1,3-bis(2,4,6-trimethylphenyl)imidazolium chloride (23 mg, 0.07 mmol), tris(dibenzylideneacetone)dipalladium (30 mg, 0.03 mmol) and cesium carbonate (925 mg, 2.8 mmol) in 1,4-dioxane (4 mL) by a procedure similar to Example 9, Step 3 yielding 16 mg (10%) of a white solid. HPLC Purity: 95%. (Reaction also yielded 106 mg (52%) of [2-(2-Methyl-6-{N′-[1-p-tolyl-ethylidene]-hydrazino}-pyrimidin-4-yl)-phenyl]-carbamic acid tert-butyl ester).

Sources & evidence

ORD record
ord-28f8244035764def937301f70a6e4562
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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