Reaction equation
C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:53]([NH2:57])[CH2:54][CH2:55][CH3:56].Br[C:59]1[CH:60]=[C:61]([CH:66]=[C:67]([Br:71])[C:68]=1[O:69][CH3:70])[C:62]([O:64][CH3:65])=[O:63]>C1(C)C=CC=CC=1.CC([O-])=O.CC([O-])=O.[Pd+2]>[Br:71][C:67]1[CH:66]=[C:61]([CH:60]=[C:59]([NH:57][CH2:53][CH2:54][CH2:55][CH3:56])[C:68]=1[O:69][CH3:70])[C:62]([O:64][CH3:65])=[O:63]Participants
7
Conditions
- Temperature
- 80 °C
Procedure
To a stirred solution of Pd(OAc)2 (144 mg), BINAP (1.2 g), and cesium carbonate (8.4 g) in toluene (100 mL) was added butylamine (1.6 mL), and the mixture was heated at 80° C. for 15 min. A solution methyl 3,5-dibromo-4-methoxybenzoate (4.2 g) in toluene (30 mL) was added dropwise over 20 min. The mixture was refluxed overnight. The mixture was cooled to room temperature, filtered through diatomaceous earth, and concentrated under reduced pressure. Purification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes) provided 3.5 g of the title compound: 1H NMR (300 MHz, CDCl3) δ 7.52, 7.19, 3.90, 3.88, 3.18, 1.66, 1.46, 0.97.
Workup
- temperatureThe mixture was refluxed overnight
- temperatureThe mixture was cooled to room temperature
- filtrationfiltered through diatomaceous earth
- concentrationconcentrated under reduced pressure
- customPurification by flash column chromatography (silica, 1:9 ethyl acetate/hexanes)
Sources & evidence
- ORD record
- ord-cb35870106e04ff18d5775ee15a2958c
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07727997B2
Linked notes
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