Acetamide → HCID 59389294, compound

HRID 2357904Notes

Reaction equation

HRID 2357904 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]([NH2:18])(=[O:17])[CH3:16].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.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]>[C:15]([NH:18][C:10]1[N:5]2[N:4]=[C:3]([CH2:1][CH3:2])[CH:14]=[C:6]2[C:7]([CH:12]=[O:13])=[CH:8][CH:9]=1)(=[O:17])[CH3:16]

Participants

8

Reactant 4

HCID 178AcetamideHCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 59389330HCID 59389330, compound

Product 1

HCID 59389294HCID 59389294, compoundYield 81.1%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

The compound of Example 130 (100 mg), acetamide (23.6 mg), tris(dibenzylideneacetone)dipalladium (15.3 mg), Xantphos (28.9 mg) and cesium carbonate (152 mg) were suspended in dioxane (3.00 mL) in an argon atmosphere. The suspension was stirred at 100° C. for 5 hours. Subsequently, the 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=5:1) to afford the title compound as a yellow powder (62.5 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=5:1)

Sources & evidence

ORD record
ord-42d9d0e1fd1849538fb9fcb36d59e735
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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