Cesium carbonate → HCID 86721322, compound

Participants

Reaction Conditions

Reaction Steps

The product from the above reaction (5-amino-2-bromo-4-fluorobenzonitrile) (4.0 g, 18.6 mmol), cyclo-propyl boronic acid (3.19 g, 37.2 mmol), Pd(OAc)2 (835 mg, 3.72 mmol), tricyclohexyl phosphine (1.04 g, 3.72 mmol), Cs2CO3 (36.3 g, 111.6 mmol) were combined in a pressure vessel. A mixture of toluene (110 ml) and H2O (35 ml) was added. The ensuing yellow-orange suspension was degassed and flushed with nitrogen gas (3×). The pressure vessel was sealed and heated over night (ca. 12 h) at 110° C. After checking the reaction by TLC and HPLC, the precipitate/salts were filtered off, more H2O was added and the mixture was extracted with ethyl acetate (3×). The combined organic phases were filtered through Na2SO4, silica gel was added and solvents were removed using a rotary evaporator. Further purification by CombiFlash (120 g column) eluting with hexanes/ethyl acetate (0→20% gradient) yielded 2.01 g (61%) of the desired product in form of a pale yellow, beige solid. 1H NMR (300 MHz, cdcl3) δ 6.98 (d, J=8.6 Hz, 1H), 6.58 (d, J=12.0 Hz, 1H), 3.81 (s br, 2H), 2.21-2.06 (m, 1H), 1.11-0.99 (m, 2H), 0.69-0.59 (m, 2H); MS (ES) 177 (M+H).

Provenance & Evidence