Reaction equation
COC(=O)c1cc(Cl)cc(B2OC(C)(C)C(C)(C)O2)c1.Nc1ccccc1>CC(C)(C)P(C(C)(C)C)C(C)(C)C.COCCOC.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=P([O-])([O-])[O-].[K+].[K+].[K+].[Pd].[Pd]>COC(=O)c1cc(Nc2ccccc2)cc(B2OC(C)(C)C(C)(C)O2)c1Participants
7
Reactant 2
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 100 °C
Procedure
aniline (0.162 mL, 1.78 mmol) was added to methyl 3-chloro-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (440mg, 1.48 mmol), TRIS(DIBENZYLIDENEACETONE)DIPALLADIUM(0) (13.59 mg, 0.01 mmol), tri- tert-butylphosphine (10.80 µL, 0.04 mmol) and potassium phosphate (441 mg, 2.08 mmol) in degassed DME (6 mL) at 20°C under nitrogen. The reaction was stirred at 100 °C for 2 days. The reaction mixture was diluted with Et2O (50 mL), and washed sequentially with water (50 mL) and saturated brine (50 mL). The organic layer was dried over MgSO4, filtered and evaporated. The crude product was purified by flash silica chromatography, elution 10 to 60% EtOAc in heptane.
Sources & evidence
- ORD record
- ord-fbf696d6dcb34e7c9c731cbe586b831a
- Source dataset
- 750 AstraZeneca ELN dataset
- Original link
- View source
Linked notes
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