ethyl 7-bromo-4-chloro-1H-indole-2-carboxylate

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

Procedure: To a solution of EXAMPLE 166B (610 mg), o-tolylboronic acid (330 mg), cesium fluoride (930 mg) in dioxane (5 mL) was added tetrakis(triphenylphosphine)palladium (240 mg). The resulting mixture was heated under reflux overnight and concentrated. The residue was diluted with ethyl acetate and saturated ammonium acetate, and the layers were separated. The aqueous layer was extracted with ethyl acetate (×2) and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (0-20% ethyl acetate in hexanes) to provide the title compound. The resulting mixture was heated under reflux overnight concentrated The residue was diluted with ethyl acetate and saturated ammonium acetate the layers were separated The aqueous layer was extracted with ethyl acetate (×2) the combined organic layers were washed with brine dried over MgSO4 filtered concentrated The residue was purified by flash chromatography (0-20% ethyl acetate in hexanes)

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

Procedure: To a solution of EXAMPLE 166B (610 mg), o-tolylboronic acid (330 mg), cesium fluoride (930 mg) in dioxane (5 mL) was added tetrakis(triphenylphosphine)palladium (240 mg). The resulting mixture was heated under reflux overnight and concentrated. The residue was diluted with ethyl acetate and saturated ammonium acetate, and the layers were separated. The aqueous layer was extracted with ethyl acetate (×2) and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (0-20% ethyl acetate in hexanes) to provide the title compound. The resulting mixture was heated under reflux overnight concentrated The residue was diluted with ethyl acetate and saturated ammonium acetate the layers were separated The aqueous layer was extracted with ethyl acetate (×2) the combined organic layers were washed with brine dried over MgSO4 filtered concentrated The residue was purified by flash chromatography (0-20% ethyl acetate in hexanes)

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

Procedure: To a solution of EXAMPLE 166B (610 mg), o-tolylboronic acid (330 mg), cesium fluoride (930 mg) in dioxane (5 mL) was added tetrakis(triphenylphosphine)palladium (240 mg). The resulting mixture was heated under reflux overnight and concentrated. The residue was diluted with ethyl acetate and saturated ammonium acetate, and the layers were separated. The aqueous layer was extracted with ethyl acetate (×2) and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (0-20% ethyl acetate in hexanes) to provide the title compound. The resulting mixture was heated under reflux overnight concentrated The residue was diluted with ethyl acetate and saturated ammonium acetate the layers were separated The aqueous layer was extracted with ethyl acetate (×2) the combined organic layers were washed with brine dried over MgSO4 filtered concentrated The residue was purified by flash chromatography (0-20% ethyl acetate in hexanes)

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

Procedure: To a solution of EXAMPLE 166B (610 mg), o-tolylboronic acid (330 mg), cesium fluoride (930 mg) in dioxane (5 mL) was added tetrakis(triphenylphosphine)palladium (240 mg). The resulting mixture was heated under reflux overnight and concentrated. The residue was diluted with ethyl acetate and saturated ammonium acetate, and the layers were separated. The aqueous layer was extracted with ethyl acetate (×2) and the combined organic layers were washed with brine, dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (0-20% ethyl acetate in hexanes) to provide the title compound. The resulting mixture was heated under reflux overnight concentrated The residue was diluted with ethyl acetate and saturated ammonium acetate the layers were separated The aqueous layer was extracted with ethyl acetate (×2) the combined organic layers were washed with brine dried over MgSO4 filtered concentrated The residue was purified by flash chromatography (0-20% ethyl acetate in hexanes)