HCID 135797785, compound → HCID 21099409, compound

HRID 2376952Notes

Reaction equation

HRID 2376952 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1/[CH:9]=[CH:10]/[C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])(=[O:19])=[O:18])=[CH:13][N:12]=1>C(OCC)(=O)C>[OH:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[F:26])(=[O:18])=[O:19])=[CH:13][N:12]=1

Participants

3

Reactant 1

HCID 135797785HCID 135797785, compound

Product 1

HCID 21099409HCID 21099409, compoundYield 14.2%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2-[(E)-2-(2-Hydroxy-4-fluorophenyl)vinyl]-5-[(2-fluorophenyl)sulfonyl]pyridine (Example 9, 55 mg, 0.15 mmol) was dissolved in ethyl acetate (3 mL) and degassed. Palladium (10% wt. on activated carbon, 15 mg) was added and the reaction stirred under a balloon of hydrogen overnight, then under a fresh balloon for 3 days. The catalyst was removed by filtration and the solvent removed in vacuo. The residue was purified by flash column chromatography on silica eluting with 2:1 isohexane:ethyl acetate to give the title compound (8 mg, 14%). δH (400 MHz, CDCl3): 9.67 (1H, s), 9.08 (1H, s), 8.25-8.22 (1H, m), 8.11-8.07 (1H, m), 7.63-7.58 (1H, m), 7.37-7.32 (2H, m), 7.15-7.09 (1H, m), 7.05-7.00 (1H, m), 6.58-6.50 (2H, m), 3.32 (2H, t, J=5.8 Hz), 3.07 (2H, t, J=6.0 Hz); m/z (ES+) 376 [MH+].

Workup

  1. customdegassed
  2. additionPalladium (10% wt. on activated carbon, 15 mg) was added
  3. waitunder a fresh balloon for 3 days
  4. customThe catalyst was removed by filtration
  5. customthe solvent removed in vacuo
  6. customThe residue was purified by flash column chromatography on silica eluting with 2:1 isohexane

Sources & evidence

ORD record
ord-f1a5d920ff9f4109b9eb78b3e3ef3c7a
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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