Dimethylformamide → HCID 67340621, compound

Participants

Reaction Conditions

Reaction Steps

Compound 8 (77 mg, 0.229 mmol), 2-chloro-N,N-diethylethanamine hydrochloride (43.3 mg, 0.252 mmol), potassium carbonate (95 mg, 0.687 mmol) and anhydrous dimethylformamide (5 mL) were charged to a small, argon purged flask fitted with a magnetic stirbar and resulting solution heated in an oil bath at 65° C. for 2 hours. After cooling to room temperature the mixture was diluted with H2O and ethyl acetate, transferred to a separatory funnel and the organic layer collected. The aqueous layer was further extracted with ethyl acetate and the combined organic layers were washed with brine (twice), dried over magnesium sulphate, filtered and concentrated to afford crude solid. The crude product was purified via chromatography on silica gel (2M NH3 in MeOH:CH2Cl2, 2.5:97.5) to yield compound 9 (79 mg, 79.2%) as a yellow solid. 1H NMR (DMSO-d6) δ 0.77 (t, 6H, J=7.1 Hz), 2.39 (q, 4H, J=7.2 Hz), 2.50 (m, 2H), 4.19 (t, 2H, J=6.5 Hz), 4.31 (s, 2H), 6.40 (s, 1H), 7.33-7.41 (m, 4H), 7.58 (d, 1H, J=9.1 Hz), 7.99 (dd, 1H, J=9.0, 2.2 Hz), 8.48 (d, 1H, J=2.3 Hz).

Provenance & Evidence