Benzoic acid, 2-iodo-, methyl ester → HCID 118131433, compound

Participants

Reaction Conditions

Reaction Steps

Pd(Ph3P)4 (683 mg, 0.591 mmol), CuI (938 mg, 49.2 mmol), methyl 2-iodobenzoate (25.8 g, 98.49 mmol), tert-butyl but-3-yn-2-ylcarbamate (intermediate 3.2, 25 g, 147.75 mmol) in DMF (30 ml) and Et3N (27 ml) were mixed in DMF (125 ml) and the mixture was heated to 60° C. under nitrogen atmosphere for 12 hrs. The mixture was quenched with water and the product extracted with EtOAc. The collected organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure. The residual was purified by column chromatography over silica gel (Hex/EtOAc 9:1) to give the title compound (15.3 g, 51%).

Provenance & Evidence