Acetic Acid → 2-(1-(4-Bromobenzyl)-5-methoxy-2-methyl-1 H-indol-3-yl) benzoic acid

Participants

Reaction Conditions

Reaction Steps

A solution of the hydrazine from Example 1, Step 5, (675 mg, 2.2 mmol), 2-(2-oxopropyl)benzoic acid (425 mg, 2.4 mmol) and acetic acid (314 μL, 5.5 mmol) in toluene was warmed to 65° C. for 1-- h after what the mixture was evaporated and acetic acid was removed with the help of heptane in vacuo. To a portion of the residue (100 mg) in dioxane (1 mL) was added 4M HCl in dioxane (2 mL) and the mixture was heated to 65° C. for 1 h. It was then cooled to 25° C. and poured on a mixture of ice water and ethyl acetate. The organic layer was washed with brine and dried with MgSO4. Removal of the solvents yielded a residue which was purified by flash chromatography. The remaining portion of the intermediate was processed identically and combined to give the product (357 mg). Anal. Calcd. for C24H20BrNO3 : C, 64.01; H, 4.48; N, 3.11. Found: C, 63.92; H, 4.51; N, 3.04.

Provenance & Evidence