p-Fluoronitrobenzene → HCID 58914732, compound

Participants

Reaction Conditions

Reaction Steps

Dissolve 1-(2-chloro-benzyl)-3-(4-methoxy-3,5-dimethyl-phenyl)-1,3-dihydro-indol-2-one (222 mg, 0.57 mmol) in anhydrous DMF (5 mL) under nitrogen. Cool in an ice bath and add at 5-8° C. a 0.5M solution of potassium bis(trimethylsilyl)amide (1.2 mL, 0.6 mmol). After 10 min. remove the ice bath and allow to warm to 20° C. over 30 min. Add 1-fluoro-4-nitrobenzene (0.21 mL, 2 mmol) and heat at 80° C. for 3 h. Allow to cool to room temperature and partition between saturated NH4Cl solution (25 mL) and ethyl acetate (50 mL). Separate, dilute aqueous portion with water (25 mL) and extract with ethyl acetate (2×50 mL). Combine all organic portions and wash with 1N HCl (50 mL) and brine (50 mL). Dry (MgSO4), filter and concentrate in vacuo to give 704 mg of a yellow oil. Purify by flash chromatography (gradient of 50% hexanes/CH2Cl2 to 100% CH2Cl2) to give 259 mg (89%) of the title compound as a light yellow foam. MS (FAB, M+1): calcd for C30H25ClN2O4 513.1581. found 513.1577; 1H NMR(DMSO-d6): □8.23 (m, 2H), 7.55-4.63 (m, 4H), 7.35-7.27 (m, 3H), 7.16 (t, J=7.5, 6.8 Hz, 1H), 7.02 (m, 2H), 6.86 (s, 2H), 5.11 (s, 2H), 3.65 (s, 3H), 2.16 (s, 6H). Anal. Calcd for C30H25ClN2O4: C, 70.24; H, 4.91; N, 5.47. Found C, 70.05; H, 5.19; N, 5.42.

Provenance & Evidence