Methanol → HCID 21099520, compound

Participants

Reaction Steps

2-Chloro-6-[2-(2,4-difluorophenyl)ethyl]-3-(phenylsulfonyl)pyridine (Example 43 Step 3, 0.21 g, 0.53 mmol) and potassium hydroxide (90 mg, 1.60 mmol) were stirred in refluxing methanol (10 ml) for 6 hours. The cooled reaction mixture was diluted with water and extracted with ethyl acetate (×2). The combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo while loading onto silica. Dry flash chromatography using 10-15% ethyl acetate/isohexane gave the title compound as a colourless gum (150 mg, 72%). δH (500 MHz, d6 DMSO): 8.25 (1H, d, J=7.7 Hz), 7.88 (2H, d, J=7.5 Hz), 7.69 (1H, t, J=7.4 Hz), 7.60 (2H, t, J=7.7 Hz), 7.27 (1H, q, J=8.0 Hz), 7.13-7.07 (2H, m), 6.94 (1H, td, J=2.1, 8.5 Hz), 3.78 (3H, s), 2.99-2.59 (4H, m); m/z (ES+) 390 [MH+].

Provenance & Evidence