Potassium trimethylsilanolate → HCID 178504667, compound

Participants

Reaction Steps

Potassium trimethylsilanolate (278 mg, 2.16 mmol) was added to a tetrahydrofuran (3 mL) solution of ethyl trans-4-({6-chloro-5-[4′-(methylsulfonyl)biphenyl-4-yl]-1H imidazo[4,5-b]pyridin-2-yl}oxy)cyclohexanecarboxylate (240 mg, 0.43 mmol), and the mixture was stirred at rt for 16 h. The reaction mixture was partitioned between EtOAc and 10% aqueous citric acid. The organic layer was separated, washed with brine, dried over magnesium sulfate and concentrated. Trituration of the resulting crude product with acetonitrile (10 mL) provided the title compound as an off-white solid. LC-MS: calculated for C26H24ClN3O5S 526.0, observed m/e: 526.3 (M+H)+ (Rt 0.8/2 min). 1H NMR δ (ppm) (DMSO-d6): 8.03-7.99 (5 H, m), 7.86 (2 H, d, J=8.16 Hz), 7.79 (2 H, d, J=8.12 Hz), 5.01-4.97 (1 H, m), 2.30 (1 H, m), 2.24 (3 H, d, J=10.17 Hz), 2.00 (3 H, m), 1.58-1.49 (4 H, m).

Provenance & Evidence