Reaction equation
CCOC(=O)c1cc2cccc(Br)c2o1.c1ccc(CCN2CCNCC2)nc1>C1COCCO1.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C(/C=C/c1ccccc1)/C=C/c1ccccc1.O=C([O-])[O-].[Cs+].[Cs+].[Pd].[Pd]>CCOC(=O)c1cc2cccc(N3CCN(CCc4ccccn4)CC3)c2o1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 95 °C
Procedure
17/02 2009 12:47:13 +0100 To ethyl 7-bromobenzofuran-2-carboxylate (1.50 g, 5.57 mmol) and 1-(2-(pyridin-2-yl)ethyl)piperazine (1.120 g, 5.85 mmol) in dry degassed dioxane (20 mL) were added Cesium carbonate (2.361 g, 7.25 mmol), 2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.266 g, 0.56 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.255 g, 0.28 mmol) under argon and the reaction heated at 95°C o/n. The reaction was allowed to reach rt. Starting material left 18/02 2009 14:51:20 +0100 Additional2-Dicyclohexylphosphino-2',4',6'-triisopropylbiphenyl (0.266 g, 0.56 mmol) and Tris(dibenzylideneacetone)dipalladium(0) (0.255 g, 0.28 mmol) were added and the reaction stirred at 95°C o/n. The reaction mixture was pooled with the reaction mixture in EN02198-44. Water and DCM were added and the layers separated. The aq phase was extracted with DCM (3x). The combined org phases were washed with water, dried (Na2SO4), filtered and evaporated. The crude was purified by flash chrom. (SiO2; DCM/MeOH 95/5) to give 1.48 g (35% calculated from EN02198-44+45) of the product as a pale brown solid.
Sources & evidence
- ORD record
- ord-3e4ae9ef9d2f47b2b03f41aafafa9bc4
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Linked notes
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