Cesium carbonate → 1552271-08-5

Participants

Reaction Conditions

Reaction Steps

5-amino-2-bromobenzonitrile (5.0 g, 25.4 mmol), cyclopropylboronic acid (4.36 g, 50.8 mmol), Cs2CO3 (49.62 g, 152.3 mmol), and tricyclohexylphosphine (2.85 g, 10.2 mmol) were weighed out and added to a large reaction tube with magnetic stir bar. Toluene (120 mL) and water (40 mL) were added, and the reaction was subjected to vigorous sub-surface nitrogen sparging. Pd(OAc)2 (1.14 g, 5.1 mmol) was weighed out and added, the tube was sealed under nitrogen, and the reaction was heated overnight at 110° C. This was then filtered with water and ethyl acetate washings. The combined washings were treated with saturated aqueous NaHCO3 and the layers were separated. The aqueous was extracted 4 more times with ethyl acetate, and the combined organic layer was washed twice with brine and dried over sodium sulfate. After filtration, concentration, and drying on the high vacuum, 7.65 g was obtained of 5-amino-2-cyclopropylbenzonitrile containing tricyclohexylphosphine derived byproducts. This was used without further purification.

Provenance & Evidence