Acetic Acid → HCID 21099514, compound

HRID 2376956Notes

Reaction equation

HRID 2376956 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[CH:16]=[CH:15][C:14](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][C:22]([F:25])=[CH:21][CH:20]=3)=[CH:13][N:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.C(O)(=O)C.[H][H]>C(OCC)(=O)C.[Pd]>[F:25][C:22]1[CH:21]=[CH:20][C:19]([CH2:18][CH2:17][C:14]2[CH:15]=[CH:16][C:11]([S:8]([C:5]3[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=3)(=[O:10])=[O:9])=[N:12][CH:13]=2)=[CH:24][CH:23]=1

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 21099448HCID 21099448, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 21099514HCID 21099514, compoundYield 17.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

2-[(4-Fluorophenyl)sulfonyl]-5-[(E)-2-(4-fluorophenyl)vinyl]pyridine (Example 37, 0.11 g, 0.308 mmol) and palladium (10% wt. on activated carbon, 32 mg) were suspended in ethyl acetate (5 mL) and acetic acid (5 mL) and shaken in a Parr apparatus at 50 psi hydrogen for 2 days. The catalyst was removed by filtration, fresh catalyst (80 mg) added and shaking at 50 psi hydrogen continued for 10 days. The catalyst was removed by filtration and the solvent removed in vacuo. The residue was partitioned between saturated sodium carbonate solution and ethyl acetate. The aqueous phase was extracted with further portions of ethyl acetate and the combined organic layers were washed with brine, dried over MgSO4 and concentrated in vacuo. The residue was purified by mass-triggered preparative HPLC (Nebula) to give the title compound as a beige solid (19 mg, 17%). δH (500 MHz, d6 DMSO): 8.52 (1H, s), 8.10 (1H, d, J=8.0 Hz), 8.02-7.99 (2H, m), 7.95 (1H, dd, J=1.9, 8.0 Hz), 7.46 (2H, t, J=8.8 Hz), 7.21 (2H, dd, J=5.7, 8.4 Hz), 7.05 (2H, t, J=8.9 Hz), 2.97-2.94 (2H, m), 2.89-2.85 (2H, m); m/z (ES+) 360 [MH+].

Workup

  1. customThe catalyst was removed by filtration, fresh catalyst (80 mg)
  2. additionadded
  3. customThe catalyst was removed by filtration
  4. customthe solvent removed in vacuo
  5. customThe residue was partitioned between saturated sodium carbonate solution and ethyl acetate
  6. extractionThe aqueous phase was extracted with further portions of ethyl acetate
  7. washthe combined organic layers were washed with brine
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by mass-triggered preparative HPLC (Nebula)

Sources & evidence

ORD record
ord-51c729344785480eae7dd3e6d4a3ed1e
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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