Potassium Hydroxide → 3-(1-Phenylsulfonyl-4-[2-(3-fluoro-phenyl)-vinyl]-1h-pyrazol-3-yl)-pyridine

HRID 1027543Notes

Reaction equation

HRID 1027543 reaction equation
[C:1]1([S:7]([N:10]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[C:12]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[N:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-].[K+].NN.O>C(O)COCCO>[F:23][C:19]1[CH:18]=[C:17]([CH:16]=[CH:15][C:13]2[C:12]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[N:11][NH:10][CH:14]=2)[CH:22]=[CH:21][CH:20]=1.[C:1]1([S:7]([N:10]2[CH:14]=[C:13]([CH:15]=[CH:16][C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=3)[C:12]([C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[N:11]2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 672850093-(1-Phenylsulfonyl-4-[2-(3-fluoro-phenyl)-vinyl]-1h-pyrazol-3-yl)-pyridine

Product 2

HCID 672850093-(1-Phenylsulfonyl-4-[2-(3-fluoro-phenyl)-vinyl]-1h-pyrazol-3-yl)-pyridineHCID 1785056723-{4-[2-(3-Fluor-phenyl)-vinyl]-1h-pyrazol-3-yl}-pyridine

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

Compound 46B (1.06 g, 2.62 mmol), 1.3 g of KOH and 2 ml NH2NH2.H2O were combined in diethylene glycol (25 ml) and warmed to reflux for 1 hour under N2. The mixture was cooled, concentrated and redissolved in MeOH. Filtration over 25 g of SCX-2 (MeOH followed by 1 N NH3/MeOH) and subsequent purification by flash chromatography (ethyl acetate) afforded 3-{4-[2-(3-fluor-phenyl)-vinyl]-1H-pyrazol-3-yl}-pyridine (the deprotected analog of 46B). Yield 0.42 g (60.4%). 1H-NMR (400 MHz, CDCl3): δ 8.85 (d, J=2 Hz, 1H), 8.65 (dd, J=5 Hz, 2 Hz, 1H), 7.95-7.90 (m, 2H), 7.45-7.41 (m, 1H), 7.32-7.27 (m, 1H), 7.20-7.16 (m, 1H), 7.14-7.09 (m, 1H), 6.99 (d, J=16 Hz, 1H), 6.96-6.86 (m, 2H).

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 1 hour under N2
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. dissolutionredissolved in MeOH
  6. filtrationFiltration
  7. customover 25 g of SCX-2 (MeOH followed by 1 N NH3/MeOH) and subsequent purification by flash chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-45731141e6d749128b8f59c42cf1437e
Source dataset
uspto-grants-2014_05
Patent number
US08735388B2

Reaction notes

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