5-Benzyl-2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine → 2-(4-Fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-A]pyrazine

HRID 920709Notes

Reaction equation

HRID 920709 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]2[N:14]=[C:15]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH:16]=[C:10]2[CH2:9]1)C1C=CC=CC=1>CO.[Pd]>[F:23][C:20]1[CH:19]=[CH:18][C:17]([C:15]2[CH:16]=[C:10]3[CH2:9][NH:8][CH2:13][CH2:12][N:11]3[N:14]=2)=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 1180613795-Benzyl-2-(4-fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine

Product 1

HCID 726989552-(4-Fluorophenyl)-4,5,6,7-tetrahydropyrazolo[1,5-A]pyrazineYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a degassed solution of Intermediate 1E (17 g, 55.3 mmol) in methanol (170 mL) was added 10% palladium on carbon (2.94 g, 2.77 mmol) and stirred under H2 atmospheric pressure for 3 h. The reaction mixture was filtered through CELITE® pad, washed with methanol (500 mL) and concentrated. The residue was triturated with diethyl ether (2×100 mL) and the resulting solid was filtered, rinsed with diethyl ether (200 mL) and dried under vacuum to afford Intermediate 1F (9 g, 75%). MS(ES): m/z=218 [M+H]+; 1H NMR (300 MHz, DMSO-d6) δ ppm 7.73-7.87 (m, 2H), 7.13-7.28 (m, 2H), 6.43 (s, 1H), 4.02 (t, J=5.57 Hz, 2H), 3.94 (s, 2H), 3.16 (t, J=5.57 Hz, 2H).

Workup

  1. filtrationThe reaction mixture was filtered through CELITE® pad
  2. washwashed with methanol (500 mL)
  3. concentrationconcentrated
  4. customThe residue was triturated with diethyl ether (2×100 mL)
  5. filtrationthe resulting solid was filtered
  6. washrinsed with diethyl ether (200 mL)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-ef349b226e0646a3b9e6be55835a48dc
Source dataset
uspto-grants-2016_03
Patent number
US09273058B2

Reaction notes

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