Cesium carbonate → HCID 67155365, compound
Reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[C:4]([Br:9])[C:3]=1[F:10].[NH:11]1[CH2:15][CH2:14][CH2:13][C:12]1=[O:16].C([O-])([O-])=O.[Cs+].[Cs+].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>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]>[Br:9][C:4]1[C:3]([F:10])=[C:2]([N:11]2[CH2:15][CH2:14][CH2:13][C:12]2=[O:16])[CH:7]=[CH:6][C:5]=1[F:8]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
1,3-dibromo-2,4-difluoro-benzene (5 g, 18.5 mmol) and pyrrolidin-2-one (1.56 g, 18.5 mmol) in dioxane (160 ml) were stirred under argon. Cs2CO3 (7.19 g, 22 mmol), xantphos (1.27 g, 2 mmol) and Pd2(dba)3 (0.675 g, 0.5 mmol) were added and the reaction was heated to 85° C. for 16 h. The reaction was quenched by the addition of 150 ml of H2O. After extraction with ethyl acetate (three times), the combined organic layers were washed with water, dried with Na2SO4, evaporated to dryness and the product was purified by silica gel chromatography (ethyl acetate/cyclohexane 0 to 20% ethyl acetate). Yield: 1 g, 20
Workup
- customThe reaction was quenched by the addition of 150 ml of H2O
- extractionAfter extraction with ethyl acetate (three times)
- washthe combined organic layers were washed with water
- dry with materialdried with Na2SO4
- customevaporated to dryness
- customthe product was purified by silica gel chromatography (ethyl acetate/cyclohexane 0 to 20% ethyl acetate)
Sources & evidence
- ORD record
- ord-e43383b792764168a7e9250fda6464a4
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08378092B2
Reaction notes
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