Water → 2-{[3-(Azidomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile

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Reaction Conditions

Reaction Steps

2-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile (2.00 g, 5.32 mmol) and sodium azide (0.346 g, 5.32 mmol) were combined in DMSO (10 mL) and stirred 16 h at 25° C. at which time TLC indicated complete conversion (10% Et2O/hexanes). Water (150 mL) and saturated aqueous NaHCO3 (30 mL) were added and the mixture stirred vigorously for 30 min. The resultant precipitate was filtered off, washed with water, and air dried to give 2-{[3-(azidomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile (1.76 g, 5.21 mmol, 98% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.01 (d, J=0.73 Hz, 1H), 7.96 (d, J=0.73 Hz, 1H), 7.48-7.60 (m, 2H), 4.60 (s, 2H).

Provenance & Evidence