4-bromo-N-cyclopropylbenzamide

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A solution of (S)-2-[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenylcarbamoyl]-pyrrolidine-1-carboxylic acid benzyl ester (74 mg, 0.16 mmol), 4-bromo-N-cyclopropyl-benzamide (39.7 mg, 0.17 mmol), and Pd[P(Ph)3]4 (13.7 mg, 7.2 mol %) in methanol (2 mL), NaHCO3 (sat. aq., 300 μL), and DMF (400 μL) was degassed and heated to 70° C. overnight in a sealed vial. The reaction was cooled, filtered, and purified by reverse phase HPLC to give the desired product. Yield 5.3 mg. MS: 484.2 (M+H+); H1 NMR (DMSO-d6): δ (ppm) 0.51-0.70 (m, 4H), 1.76-1.98 (m, 3H), 2.08-2.30 (m, 1H), 2.77-2.86 (m, 1H), 3.38-3.52 (m, 2H), 4.27-4.37 (m, 1H), 4.86-5.08 (m, 2H), 6.96-7.65 (m, 7 The reaction was cooled filtered purified by reverse phase HPLC

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

Procedure: 4-Bromo-benzoic acid (2.5116 g, 12.5 mmol) and HATU (5.2213 g, 13.7 mmol) were dissolved in DMF (40 mL). DIEA (4.572 mL, 26.2 mmol) was added, and the mixture was allowed to stir at ambient temperature for 15 minutes. Then cyclopropylamine (0.866 mL, 12.5 mmol) was added, and the reaction was stirred at ambient temperature overnight. The solvent was removed, and the crude was purified via silica gel chromatography to give the desired product. the reaction was stirred at ambient temperature overnight The solvent was removed the crude was purified via silica gel chromatography