Dimethyl Sulfoxide → 1-(4-Methoxyphenyl)-3-methanesulfonyl-6-{4-[1-(2-oxo-pyrrolidin-1-ylmethyl)cyclopropyl]phenyl}-1,4,5,6-tetrahydro-pyrazolo[3,4-c]pyridin-7-one

Participants

Reaction Conditions

Reaction Steps

Part C. The product from Part B (0.18 g, 0.56 mmol) and 1-(4-methoxyphenyl)-3-(methylsulfonyl)-1,4,5,6-tetrahydro-7H-pyrazolo[3,4-c]pyridin-7-one (0.16 g, 0.47 mmol) were stirred in DMSO (1 mL) under N2. K2CO3 (0.20 g, 1.44 mmol) was added, followed by the addition of CuI (0.030 g, 20 mol %) and 1,10-phenanthroline (0.028 g, 20 mol %). The resulting mixture was heated at 120° C. overnight. After cooling, it was extracted with EtOAc (2×), washed with H2O and brine, dried over MgSO4, filtered, and concentrated to dryness. The residue was purified by flash column chromatography (silica gel, CH2Cl2:EtOAc 1:1, then EtOAc) to give the desired compound (83 mg, yield: 25%). LC/MS (ESI+) 535.2 (M+H)+, tR=3.45 min (10–90% CH3CN/H2O in a 6-min run). 1H NMR (CDCl3) δ 7.45 (d, J=8.8 Hz, 2H), 7.25 (AA′BB′, J=8.6 Hz, 4H), 6.91 (d, J=9.2 Hz, 2H), 4.10 (t, J=6.6 Hz, 2H), 3.80 (s, 3H), 3.68 (s, 2H), 3.46 (m, 2H), 3.29 (m, 3H), 3.23 (t, J=6.6 Hz, 2H), 2.25 (m, 2H), 1.86 (m, 2H), 0.86 (m, 4H) ppm.

Provenance & Evidence