Cesium carbonate → [2-Chloro-4-(2-nitro-phenylamino)-phenyl]-{2-methyl-4-[2-(tetrahydro-pyran-2-yloxy)-ethoxy]-phenyl}-methanone

Participants

Reaction Conditions

Reaction Steps

1-Iodo-2-nitro-benzene (1.38 g, 5.54 mmol) was dissolved in 40 mL dry 1,4-dioxane under an argon atmosphere. Compound 471 (1.77 g, 4.54 mmol) was added and dissolved in the solvent. Rac-BINAP (106 mg, 0.17 mmol), Pd2(dba)3 (104 mg, 0.11 mmol) and Cs2CO3 (2.07 g, 6.30 mmol) were added, and the reaction mixture was stirred under an argon atmosphere at 100° C. for 24 h. The reaction mixture was poured into a mixture of EtOAc and water. The aqueous phase was washed with more EtOAc. The organic phases were combined and washed with brine, dried (MgSO4), filtered and then purified by flash chromatography using EtOAc/petroleum ether 1:5 as the eluent to afford the title compound.

Provenance & Evidence