Potassium Carbonate → HCID 44525560, compound

Participants

Reaction Conditions

Reaction Steps

K2CO3 aqueous solution (1 M, 5.4 mL) was added to a suspension of 5-bromo-3-(6-methoxypyridin-3-yl)pyridin-2-amine (1.44 g, 5.14 mmol), 4-(methylsulfonyl)phenyl boronic acid (1.08 g, 5.40 mmol, 1.05 equiv.), and Pd(PPh)3 (300 mg, 5 mol %) in dioxane (15 mL) under N2. The reaction mixture was stirred at 120° C. for 14 h, poured onto H2O (50 mL) and extracted with EtOAc (3×100 mL). The combined organic layers were washed with brine, dried over anhydrous MgSO4 and concentrated in vacuo. The residue was purified by column chromatography on silica gel (hexane/EtOAc, 2/8) providing 3-(6-methoxypyridin-3-yl)-5-(4-methylsulfonylphenyl)pyridin-2-amine (1) (1.92 g, 65%) as a pale yellow solid. IR (thin film/cm−1): νmax 3378, 1594, 1301, 1148. H1 NMR (400 MHz, CDCl3): δ 8.34 (d, 1H, J=2.0 Hz), 8.26 (d, 1H, J=2.0 Hz), 7.97 (d, 2H, J=8.4 Hz), 7.70 (d, 2H, J=8.4 Hz), 7.69 (d, 1H, J=8.4 Hz), 7.58 (d, 1H, J=2.0 ), 6.86 (d, 1H, J=8.4 Hz), 4.80 (bs, 2H), 3.98 (s, 3H) and 3.06 (s, 3H). C13 NMR (100 MHz, CDCl3): δ 164.16, 156.30, 146.94, 146.82, 145.57, 143.34, 139.02, 138.86, 136.92, 128.17, 126.84, 125.84, 118.88, 111.49, 53.67 and 44.62.

Provenance & Evidence