HCID 87332960, compound → HCID 58851478, compound

Participants

Reaction Conditions

Reaction Steps

To this aldehyde (150 mg, 0.312 mmol) in THF (5 mL) at 0° C. was added dropwise MeMgCl (0.37 mL, 82 mg, 1.09 mmol). The mixture was stirred at 0° C. for 1 h and then warmed to RT and stirred for 7 h. The mixture was treated with an additional batch of MeMgCl (0.2 mL, 0.6 mmol), stirred overnight at RT, treated with additional MeMgCl (0.3 mL, 0.9 mmol) and then quenched with H2O (25 mL) and diluted with EtOAc (25 mL) and 5% citric acid (10 mL). The organic phase was separated, washed with brine dried (Na2SO4), filtered, concentrated and purified to yield 1-(3-t-butyl-1-(4-(1-hydroxyethyl)naphthalen-2-yl)-1H-pyrazol-5-yl)-3-(2,3-dichlorophenyl)urea (65 mg, 42% yield). 1H-NMR (300 MHz, DMSO-d6): δ 1.31 (s, 9H), 1.49 (d, J=6.2 Hz, 3H), 5.47-5.48 (m, 1H), 5.53-5.54 (m, 1H), 6.45 (s, 1H), 7.28-7.31 (m, 2H), 7.57-7.60 (m, 2H), 7.83 (s, 1H), 7.94 (s, 1H), 8.02-8.18 (m, 3H), 8.78 (s, 1H), 9.31 (s, 1H); MS (ESI) m/z: 499.0 (M+H+).

Provenance & Evidence