Benzenesulfonyl chloride → 5-(2-Fluoropyridin-3-yl)azepan-2-one

HRID 1880117Notes

Reaction equation

HRID 1880117 reaction equation
C1(S(Cl)(=O)=[O:8])C=CC=CC=1.[F:11][C:12]1[C:17]([CH:18]2[CH2:23][CH2:22][C:21](=[N:24]O)[CH2:20][CH2:19]2)=[CH:16][CH:15]=[CH:14][N:13]=1>N1C=CC=CC=1>[F:11][C:12]1[C:17]([CH:18]2[CH2:23][CH2:22][NH:24][C:21](=[O:8])[CH2:20][CH2:19]2)=[CH:16][CH:15]=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 7369Benzenesulfonyl chlorideHCID 59326817HCID 59326817, compound

Product 1

HCID 593268345-(2-Fluoropyridin-3-yl)azepan-2-one

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

Benzenesulfonyl chloride (0.05 mL, 0.40 mmol) was added to a solution of 4-(2-fluoropyridin-3-yl)cyclohexanone oxime (0.075 g, 0.36 mmol) in pyridine (1 mL) at 0° C. The ice bath was removed and the mixture was stirred for 45 min before being heated to 100° C. for 30 minutes. After cooling to room temperature the pyridine was removed in vacuo and the residue was dissolved in 1:1 dioxane/water (5 mL) and stirred overnight. Ammonium chloride (50 mg) was added and stirring continued for 30 minutes. The mixture was extracted with ethyl acetate (3×), the combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo. The resulting oil was purified by silica gel chromatography to 5-(2-fluoropyridin-3-yl)azepan-2-one. [M+1]=209.1.

Workup

  1. customThe ice bath was removed
  2. temperatureAfter cooling to room temperature the pyridine
  3. customwas removed in vacuo
  4. dissolutionthe residue was dissolved in 1:1 dioxane/water (5 mL)
  5. stirringstirred overnight
  6. additionAmmonium chloride (50 mg) was added
  7. stirringstirring
  8. waitcontinued for 30 minutes
  9. extractionThe mixture was extracted with ethyl acetate (3×)
  10. dry with materialthe combined extracts were dried over anhydrous magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo
  13. customThe resulting oil was purified by silica gel chromatography to 5-(2-fluoropyridin-3-yl)azepan-2-one

Sources & evidence

ORD record
ord-a381329915074c9ea1c87650dd2101b0
Source dataset
uspto-grants-2012_11
Patent number
US08318718B2

Reaction notes

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