1,2-Dimethoxyethane → HCID 72202747, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-iodo-N-(4-(trifluoromethoxy)phenyl)benzamide (Stage 1.1, 550 mg, 1.351 mmol), pyrimidin-5-ylboronic acid (418 mg, 3.38 mmol), Na2CO3 (716 mg, 6.75 mmol), DME (6304 μL), water (1801 μL) and EtOH (901 μL) was stirred at 80° C. for 1 h. THF (5 mL) was added and the mixture was treated with Si-Thiol (938 mg, 1.351 mmol), stirred for 2 h and filtered through Florisil®. The filtrate was evaporated to dryness under reduced pressure and the residue was purified by flash chromatography (Biotage Silica gel column, 25 g, cyclohexane/EtOAc, from 20% to 75% EtOAc) to yield the title compound as a white solid. UPLC-MS (Condition 1) tR=360.0 [M+H]+, m/z=358.1 [M−H]−; 1H-NMR (400 MHz, DMSO-d6) δ ppm 7.40 (m, J=8.3 Hz, 2H) 7.72 (t, 1H) 7.91 (m, J=8.6 Hz, 2H) 7.98-8.11 (m, 2H) 8.36 (br. s, br. s, 1H) 9.19-9.31 (m, 3H) 10.52 (br. s, br. s, 1H).

Provenance & Evidence