1,3-Cyclopentanedione → 4-(3-Bromo-4-fluorophenyl)-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dione

HRID 1837046Notes

Reaction equation

HRID 1837046 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[NH:5][C:4](=[O:8])[CH:3]=1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[CH:16][C:17]=1[F:18])[CH:13]=O.[C:19]1(=O)[CH2:23][CH2:22][C:21](=[O:24])[CH2:20]1>C(O)C>[Br:9][C:10]1[CH:11]=[C:12]([CH:13]2[C:3]3[C:4](=[O:8])[NH:5][N:6]([CH3:7])[C:2]=3[NH:1][C:19]3[CH2:23][CH2:22][C:21](=[O:24])[C:20]2=3)[CH:15]=[CH:16][C:17]=1[F:18]

Participants

5

Reactant 3

HCID 774661,3-CyclopentanedioneHCID 1736043-Bromo-4-fluorobenzaldehydeHCID 2521985-amino-1-methyl-2,3-dihydro-1H-pyrazol-3-one

Product 1

HCID 101342284-(3-Bromo-4-fluorophenyl)-1-methyl-1,2,4,6,7,8-hexahydrocyclopenta[b]pyrazolo[4,3-e]pyridine-3,5-dioneYield 79.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

5-Amino-1-methyl-1,2-dihydropyrazol-3-one (0.23 g, 2 mmol), prepared as described in (C. Taylor and J. Barton, J.Am.Chem. Soc., (1959) 81, 2448), 3-bromo-4-fluorobenzaldehyde (0.4 g, 2 mmol), and 1,3-cyclopentanedione (0.2 g, 2 mmol) in ethyl alcohol (4 mL) were heated at 80° C. for 2 days in a sealed tube. The reaction was cooled and the resulting precipitate was filtered off to provide 0.6 g (79%) of the title compound as a tan solid. 1H NMR (300 MHz, DMSO-d6) δ 2.3 (t, 2H), 2.69 (m, 2H), 3.5 (s, 3H), 4.7 (s, 1H), 7.15 (m, 1H), 7.2 (t, 1H), 7.39 (dd, 1H), 9.56 (s, 1H), 10.42 (s, 1H); MS (ESI+) m/z 380 (M+H)+; Anal. calcd for C16H13N3BrFO2.C2H6O: C, 50.96; H, 4.51; N, 9.90. Found: C, 50.51; H, 4.58; N, 9.79.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationthe resulting precipitate was filtered off

Sources & evidence

ORD record
ord-74baebbbf1f148fdb53ea5112bdaf82a
Source dataset
uspto-grants-2004_08
Patent number
US06780872B2

Reaction notes

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