Sodium hydride → HCID 178488608, compound

Participants

Reaction Steps

5-(4-Methoxyphenyl)-3-methyl-1H-pyrazole (91 mg, 0.483 mmol) was dissolved in dry DMF (2 ml). The flask was flushed with N2 and the solution was treated with NaH (BO % in mineral oil) (19.33 mg, 0.483 mmol) and stirred at RT for ˜10 mins. Trans-methanesulfonic acid 4-(2-chloro-5-trifluoromethyl-benzoylamino)-cyclohexylmethyl ester (Intermediate G) (100 mg, 0.242 mmol) was added and the mixture was heated to 50° C. for 4 hours. After cooling to RT, the mixture was diluted with EtOAc/H2O (20 ml) and transferred to a separating funnel. The organic layer was separated and washed with brine, dried (MgSO4) and concentrated in vacuo to give a brown oil. Purification of the crude product by chromatography on silica eluting with EtOAc/iso-Hexane afforded the title compound as a white solid; LCMS Rt=1.39 min, [M+H]+ 506.3; Method 2 minLC—30_v002. 1H NMR (400 MHz, CDCl3) δ 7.9 (1H, s), 7.7 (1H, d), 7.6 (1H, d), 7.55 (1H, d), 6.95 (2H, d), 6.25 (1H, s), 5.95 (1H, d), 4.0 (1H, m), 3.95 (2H, d), 3.85 (3H, s), 2.3 (3H, s), 2.2 (2H, d), 2.1 (1H, m), 1.8 (2H, d), 1.25 (4H, m).

Provenance & Evidence