Sodium Azide → HCID 86663066, compound

Participants

Reaction Steps

A mixture of methyl 4′-amino-4″-(4-methylpiperidin-1-yl)-3-trifluoromethyl-[1,1′:3′,1″-terphenyl]-5′-carboxylate (250 mg, 0.532 mmol) in hydrochloric acid, (12 mL, 37% aqueous solution) was cooled in an ice bath and a solution of sodium nitrite (220 mg, 3.19 mmol) in water (2 mL) was added slowly. The orange-red solution was stirred for 30 min and a solution of sodium azide (208 mg, 3.19 mmol) in water (2 mL) was added dropwise. After 30 min this was partitioned between DCM and water. The organic phase washed with water and the combined organic phases were basified with 10 N aq. NaOH solution. This was extracted with DCM and the organic phases were washed with sat. NaHCO3 solution, brine, and dried with sodium sulfate. Removal of the solvent followed by silica gel chromatography (step gradient elution with DCM containing 0 to 2% MeOH) afford methyl 4′-azido-4″-(4-methylpiperidin-1-yl)-3-trifluoromethyl-[1,1′:3′,1″-terphenyl]-5′-carboxylate (128 mg, 0.26 mmol, 49% yield) as a solid. 1H NMR (500 MHz, chloroform-d) δ ppm 8.02 (1H, d, J=2.44 Hz), 7.85 (1H, s), 7.79 (1H, d, J=7.63 Hz), 7.68 (1H, d, J=2.44 Hz), 7.64 (1H, d, J=7.63 Hz), 7.59 (1H, d, J=7.63 Hz), 7.42 (2H, d, J=8.55 Hz), 7.04 (2H, d, J=8.85 Hz), 4.03 (3H, s), 3.26-3.39 (4H, m), 2.57-2.69 (4H, m), 2.38 (3H, s).

Provenance & Evidence