Cesium carbonate → HCID 59389324, compound

HRID 2357905Notes

Reaction equation

HRID 2357905 reaction equation
[CH2:1]([C:3]1[CH:14]=[C:6]2[C:7]([CH:12]=[O:13])=[CH:8][CH:9]=[C:10](I)[N:5]2[N:4]=1)[CH3:2].[C:15]1(OB(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(P(CCCC)CCCC)CCC.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C(Cl)Cl.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]>[CH2:1]([C:3]1[CH:14]=[C:6]2[C:7]([CH:12]=[O:13])=[CH:8][CH:9]=[C:10]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:5]2[N:4]=1)[CH3:2]

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 13831TributylphosphineHCID 78412Phenyl dihydrogen orthoborateHCID 59389330HCID 59389330, compound

Product 1

HCID 59389324HCID 59389324, compoundYield 95.2%

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

The compound of Example 130 (50.0 mg), phenylboric acid (22.4 mg), tris(dibenzylideneacetone)dipalladium (3.1 mg), tri-n-butylphosphine (17.0 μL) and cesium carbonate (65.3 mg) were suspended in dioxane in an argon atmosphere. The suspension was stirred at 80° C. for 6.5 hours. Subsequently, the reaction mixture was diluted with methylene chloride and filtered through Celite. The filtrate was evaporated and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1) to afford the title compound as a yellow oil (38.7 mg).

Workup

  1. filtrationfiltered through Celite
  2. customThe filtrate was evaporated
  3. customthe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1)

Sources & evidence

ORD record
ord-a25131fe4e674bf8b59471108e6e60dd
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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