2-(azidomethyl)-5-chloro-1-benzofuran

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 2-(azidomethyl)-5-chloro-1-benzofuran (500 mg, 2.44 mmol) in tetrahydrofuran (10 ml) and water (1 ml) was added PPh3 (759 mg, 2.89 mmol) and the contents were stirred for 3 hours at 60° C. The resulting mixture was concentrated under vacuum to give a residue, which was purified by silica gel column chromatography eluting with methanol in dichloromethane to afford (5-chloro-1-benzofuran-2-yl)methanamine as a colorless liquid (420 mg, crude). (ES, m/z): [M+H]+ 182.0; 1H NMR (400 MHz, CDCl3): δ 7.55-7.58 (m, 1H), 7.50-7.47 (m, 1H), 7.21 (d, J=8.8 Hz, 1H), 6.50 (s, 1H), 3.99 (s, 2H). The resulting mixture was concentrated under vacuum to give a residue, which was purified by silica gel column chromatography eluting with methanol in dichloromethane

Conditions: temp:70.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 5-chloro-2-(chloromethyl)-1-benzofuran (500 mg, 2.49 mmol) in N,N-dimethylformamide (10 ml) was added NaN3 (320 mg, 4.92 mmol) and the contents were stirred overnight at 70° C. The resulting solution was diluted with saturated aqueous sodium bicarbonate (150 ml) and extracted with dichloromethane (3×70 ml). The organic layers were combined, dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum. The residue was purified by silica gel column chromatography eluting with petroleum ether to afford 2-(azidomethyl)-5-chloro-1-benzofuran as light brown oil (500 mg, 97%). 1H NMR (300 MHz, CDCl3): δ 7.54 (s, 1H), 7.40 (d, J=9.0 Hz, 1H), 7.25 (d, J=9.0 Hz, 1H), 6.66 (s, 1H), 4.50 (s, 2H). extracted with dichloromethane (3×70 ml) dried over anhydrous sodium sulfate filtered concentrated under vacuum The residue was purified by silica gel column chromatography eluting with petroleum ether