Potassium Hydroxide → 3-(1-phenylsulfonyl-4-oct-1-enyl-1H-pyrazol-3-yl)-pyridine

HRID 2043053Notes

Reaction equation

HRID 2043053 reaction equation
[C:1]1([S:7]([N:10]2[CH:14]=[C:13]([CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:12]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=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>[CH:15]([C:13]1[C:12]([C:23]2[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=2)=[N:11][NH:10][CH:14]=1)=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:1]1([S:7]([N:10]2[CH:14]=[C:13]([CH:15]=[CH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[C:12]([C:23]3[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=3)=[N:11]2)(=[O:8])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 672842033-(1-phenylsulfonyl-4-oct-1-enyl-1H-pyrazol-3-yl)-pyridine

Product 2

HCID 672842033-(1-phenylsulfonyl-4-oct-1-enyl-1H-pyrazol-3-yl)-pyridineHCID 178442670HCID 178442670, compound

Reagents, catalysts & solvents 1

HCID 8117Diethylene GlycolSolvent

Procedure

Compound 46C (0.35 g, 0.89 mmol), 0.7 g of KOH and 1 ml of NH2NH2.H2O were combined in diethylene glycol (10 ml) and warmed to reflux for 1 hour under N2. The mixture was cooled, concentrated and re-dissolved 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-oct-1-enyl-1H-pyrazol-3-yl)-pyridine (the deprotected analog of 46C). Yield 0.19 g (95%). 1H-NMR (400 MHz, CDCl3): δ 8.85 (d, J=2 Hz, 1H), 8.65 (dd, J=5 Hz, 2 Hz, 1H), 7.91 (dt, J=8 Hz, 2 Hz, 1H), 7.71 (s, 1H), 7.41-7.36 (m, 1H), 6.27 (d, J=16 Hz, 1H), 6.07-5.98 (m, 1H), 2.19-2.12 (m, 2H), 1.46-1.38 (m, 2H), 1.37-1.23 (m, 6H), 0.89 (t, J=7 Hz, 3H).

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 1 hour under N2
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. dissolutionre-dissolved 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-b2f1df5fa07042f198c210c43c9cd00e
Source dataset
uspto-grants-2013_11
Patent number
US08586606B2

Reaction notes

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