Bromotrimethylsilane → 4-(4-Bromothiazolo[5,4-c]pyridin-2-yl)-3-chloro-5-fluorobenzonitrile

Participants

Reaction Steps

A suspension of 3-chloro-4-(4-chlorothiazolo[5,4-c]pyridin-2-yl)-5-fluorobenzonitrile (0.077 g, 0.24 mmol) and trimethylsilyl bromide (63 μL 0.48 mmol) in propionitrile (2.4 mL) was heated under reflux for 5 hours before further trimethylsilyl bromide (30 μL, 0.24 mmol) was added. The resulting mixture was heated under reflux for a further 16 hours then partitioned between DCM and water. The organic layer was dried over Na2SO4 and concentrated under reduced pressure to give the desired compound as an off-white solid (0.090 g, quant. yield). 1H NMR (300 MHz, CDCl3): δ 8.53 (d, J=5.6 Hz, 1H), 8.03 (d, J=5.6 Hz, 1H), 7.72 (t, J=1.4 Hz, 1H), 7.52 (dd, J=8.3; 1.5 Hz, 1H). LCMS (Method D): RT=3.89 min, m/z: 368 [M+H+].

Provenance & Evidence