HCID 10155033, compound → HCID 9968553, compound

HRID 966451Notes

Reaction equation

HRID 966451 reaction equation
[C:1]1([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][CH:13]=3)[N:10]=[C:9]([CH:22]([F:24])[F:23])[CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]=1>C(O)C.[Pd]>[CH:1]1([C:7]2[N:11]([C:12]3[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:19])=[O:20])=[CH:14][CH:13]=3)[N:10]=[C:9]([CH:22]([F:23])[F:24])[CH:8]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 1

HCID 10155033HCID 10155033, compound

Product 1

HCID 9968553HCID 9968553, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

4-[5-(1-Cyclohexenyl)-3-(difluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (Example 142) (0.31 g, 0.88 mmol) was dissolved in ethanol (15 mL), 10% palladium on charcoal was added, and the suspension was stirred at room temperature under hydrogen (36psi) for 18.25 hours. The reaction was filtered through celite, and the ethanol removed in vacuo to give a white solid, which was recrystallized from methylene chloride/isooctane (0.31 g, 99%): mp 199-203° C.; 1H NMR (acetone-d6) 300 MHz 8.05 (d, J=8.7 Hz, 2H), 7.60 (d, J=8.5 Hz, 2H), 6.69 (t, J=55.0 Hz 1 H), 6.47 (s, 1H), 5.02 (br s, 2H), 2.67 (m, 1H), 1.71-1.88(m, 5H), 1.24-1.43 (m, 5H); 19F NMR (acetone-d6) 300 MHz: −112.86 (d).

Workup

  1. filtrationThe reaction was filtered through celite
  2. customthe ethanol removed in vacuo
  3. customto give a white solid, which
  4. customwas recrystallized from methylene chloride/isooctane (0.31 g, 99%)

Sources & evidence

ORD record
ord-ced474d76c674852adb359975f332be5
Source dataset
uspto-grants-2005_10
Patent number
US06951949B2

Reaction notes

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