Cesium carbonate → HCID 69676416, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 4-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (1.35 g, 3.70 mmol, 1.0 eq), (R)-1-(3-aminopiperidin-1-yl)-2-((3,5-dichlorophenyl)amino)ethanone (1.34 g, 4.44 mmol, 1.2 eq) in PhCH3 (10 mL) was added Pd(OAc)2 (83 mg, 0.370 mmol, 0.1 eq), xantphos (250 mg, 0.43 mmol, 0.15 eq) and Cs2CO3 (2.82 g, 8.64 mmol, 3.0 eq) and the mixture was heated at 100° C. for 16 h. The reaction was cooled to rt, filtered through Celite, and concentrated in vacuo to afford a residue which was purified by silica gel column chromatography (PE/EA=10:1) to give brown solid (451 mg, yield: 21%). 1H NMR (400 MHz, CDCl3) δ: 8.90 (d, 1H), 8.74˜8.73 (m, 1H), 8.01˜7.94 (m, 2H), 7.54˜7.48 (m, 1H), 7.21˜7.19 (m, 2H), 6.75 (d, 1H), 6.69˜6.68 (m, 1H), 6.42˜6.32 (m, 2H), 5.11˜5.10 (m, 1H), 4.42˜4.38 (m, 1H), 3.92˜3.75 (m, 5H), 3.56˜3.52 (m, 2H), 3.23˜3.20 (m, 1H), 3.09˜3.03 (m, 1H), 2.30 (m, 3H), 2.14˜2.10 (m, 1H), 1.86˜1.72 (m, 1H), 1.69˜1.57 (m, 2H). ESI-MS: 630.0 (M+H)+.

Provenance & Evidence