Water → (2R)-N-hydroxy-2-methyl-4-[4-(2-methyl-1H-indol-5-yl)-2-oxopyridin-1(2H)-yl]-2-(methylsulfonyl)butanamide

Participants

Reaction Conditions

Reaction Steps

Pd EnCat™ (93 mg, 0.03 mmol) was added to a mixture of potassium carbonate (115 mg, 0.83 mmol), 2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole (86 mg, 0.33 mmol), and (2R)—N-hydroxy-4-(4-iodo-2-oxopyridin-1(2H)-yl)-2-methyl-2-(methylsulfonyl)butanamide (115 mg, 0.28 mmol) in dioxane:water (2.5 mL, 5:1 mixture). The reaction mixture was heated overnight at 80° C. The reaction was cooled to ambient temperature, filtered through a nylon filter and concentrated. The material was dissolved in a minimal amount of DMSO and loaded onto a 13 g c18 column. The gradient was run from 25-45% acetonitrile in water. The desired material was concentrated yielding 25 mg (22%) of a light brown solid. LCMS m/z 418.5 (M+1) 1H NMR (400 MHz, DMSO-d6) δ ppm 1.58 (s, 3H) 2.13-2.24 (m, 1H) 2.32-2.46 (m, 1H) 2.39 (s, 3H) 3.12 (s, 3H) 3.69-3.78 (m, 1H) 4.06-4.16 (m, 1H) 6.20 (s, 1H) 6.65 (d, J=1.95 Hz, 1H) 6.70 (dd, J=7.22, 1.95 Hz, 1H) 7.31-7.39 (m, 2H) 7.70 (d, J=7.22 Hz, 1H) 7.79 (s, 1H) 9.25 (br. s., 1H) 11.11 (br. s., 1H) 11.23 (br. s., 1H)

Provenance & Evidence