Water → HCID 24986682, compound

Participants

Reaction Conditions

Reaction Steps

1-[1-(2-Chloro-phenyl)-ethyl]-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1,2,3,4-tetrahydro-thieno[3,2-e][1,4]diazepin-5-one (251 mg, 0.58 mmol, 1.3 Eq), 3-iodo-imidazo[1,2-a]pyridine (109 mg, 0.45 mmol, 1.0 Eq) and Pd(PPh3)4 (52 mg, 0.045 mmol, 0.1 Eq) were dissolved in toluene (1.6 mL) and EtOH (0.4 mL). 2M K2CO3 (0.45 mL, 0.89 mmol, 2.0 Eq) was added and the reaction heated at 140° C. for 15 minutes under microwave conditions. Water (10 mL) and EtOAc (15 mL) was added and the layers separated. The aqueous layer was extracted with EtOAc (3×10 mL) and the combined organic layers washed with brine (15 mL), dried (MgSO4) and concentrated in vacuo. The crude product was purified by chromatography to give the title compound as a pale yellow solid (66 mg, 0.16 mmol, 35%); 1H NMR (DMSO D6) 1.57 (3H, d), 2.92-3.00 (1H, m), 3.10-3.18 (1H, m), 3.29-3.33 (2H, m), 5.51 (1H, q), 7.12 (1H, t), 7.36-7.46 (4H, m), 7.52 (1H, d), 7.59 (1H, d), 7.69-7.75 (2H, m), 7.95 (1H, s), 8.62 (1H, d); LC/MS M+1 (obs.) 423.1, LC/MS M−1 (obs.) 421.3.

Provenance & Evidence