Methanol → HCID 21099520, compound

HRID 1351640Notes

Reaction equation

HRID 1351640 reaction equation
Cl[CH:2]([C:12]1[CH:17]=[CH:16][C:15]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:14][N:13]=1)[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][C:5]=1[F:11].[OH-:27].[K+].[CH3:29]O>O>[F:11][C:5]1[CH:6]=[C:7]([F:10])[CH:8]=[CH:9][C:4]=1[CH2:3][CH2:2][C:12]1[N:13]=[C:14]([O:27][CH3:29])[C:15]([S:18]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:20])=[O:19])=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 21099405HCID 21099405, compound

Product 1

HCID 21099520HCID 21099520, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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+].

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with ethyl acetate (×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customDry flash chromatography

Sources & evidence

ORD record
ord-ef65b9a7d3b74056a9f1b704c870a1e8
Source dataset
uspto-grants-2007_05
Patent number
US07217740B2

Reaction notes

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