tert-butyl benzoate

Conditions: temp:105.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: 4-Ethoxy-1-ethyl-1H-indole-2-carboxylic acid [4-((S)-pyrrolidin-3-yloxy)-phenyl]-amide hydrochloride (103 mg, 0.24 mmol) was mixed with 4-bromo-benzoic acid tert-butyl ester (74 mg, 0.29 mmol) in dioxane (4 mL). To this solution was added tris(dibenzylideneacetone)dipalladium (Pd2(dba)3, 20 mg), (2′,4′,6′-triisopropyl-1,1′-biphenyl-2-yl)dicyclohexylphosphine (X-PHOS, 35 mg) and sodium tert-butoxide (70 mg, 0.72 mmol). The mixture was degassed with argon and then sealed. The stirred solution was heated at 105° C. for 2 hrs and solvents were evaporated. The residue was extracted with ethyl acetate and ammonium chloride solution. The organic layer was dried over sodium sulfate and then concentrated. The residue was purified through flash column chromatography using ethyl acetate in hexanes (5% to 60%) to give a white solid as 4-(S)-3-{4-[(4-ethoxy-1-ethyl-1H-indole-2-carbonyl)-amino]-phenoxy}-pyrrolidin-1-yl)-benzoic acid tert-butyl ester (100 mg). The mixture was degassed with argon sealed solvents were evaporated The residue was extracted with ethyl acetate and ammonium chloride solution The organic layer was dried over sodium sulfate concentrated The residue was purified through flash column chromatography

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of 0.74 g. of t-butanol, 1.22 g. of benzoic acid, 3.32 g. of 2,2'-dibenzothiazolyl disulfide and 50 ml. of methylene chloride is added dropwise a solution of 2.62 g. of triphenyl phosphine in 20 ml. of methylene chloride while stirring at room temperature. After completion of the addition, the mixture is stirred at room temperature for an additional 5 hours. The reaction mixture is treated with the same procedure as in Example 1 (1) to give 1.35 g. of the desired product boiling at 75°C/3 mmHg. To a mixture of 0.74 g After completion of the addition to give 1.35 g