Acetic Acid → HCID 178490616, compound

Participants

Reaction Steps

A solution of (R)-4-[1-(3-cyclopentyloxy-4-methoxyphenyl)-2-(4-pyridyl)ethyl]benzene-nitrile from Step 1 (350 mg, 0.88 mmol) and tributyltin azide (1.17 g, 3.5 mmol) in 1,2-dichlorobenzene (4 mL) was stirred at 150° C. for 2 hours. The reaction mixture was then cooled to room temperature and acetic acid (0.5 mL) was added. After 15 min, aqueous 1N NaOH was added and the aqueous phase was washed 3 times with ether. The aqueous phase was then treated with 25% aqueous NH4OAc and 6N HCl to pH 7 before it was extracted twice with CH2Cl2. The organic phase was then dried (MgSO4) and evaporated to afford the title compound as a yellow solid (341 mg, 88%). 1H NMR (400 MHz, CDCl3): d 1.55 (m, 2H), 1.80 (m, 6H), 3.30 (m, 1H), 3.45 (m, 1H), 3.80 (s, 3H), 4.20 (m, 1H), 4.70 (m, 1H), 6.70 (s, 1H), 6.80 (m, 2H), 7.00 (d, 2H), 7.20 (d, 2H), 7.90 (d, 2H), 8.40 (d, 2H).

Provenance & Evidence