HCID 68153800, compound → HCID 69935042, compound

HRID 341107Notes

Reaction equation

HRID 341107 reaction equation
[CH2:1]([N:4]1[C:24](=[O:25])[C:7]2=[CH:8][N:9]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]2=[N:5]1)[CH:2]=[CH2:3]>CO.[Pd]>[F:23][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][N:9]2[C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:15]=3[C:6]3=[N:5][N:4]([CH2:1][CH2:2][CH3:3])[C:24](=[O:25])[C:7]3=[CH:8]2)=[CH:22][CH:21]=1

Participants

4

Reactant 1

HCID 68153800HCID 68153800, compound

Product 1

HCID 69935042HCID 69935042, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Allyl-5-(4-fluorobenzyl)-2,5-dihydro-3H-pyrazolo[4,3-c]quinolin-3-one (Example 764, 20 mg, 0.060 mmol) was dissolved in methanol (3 mL), treated with palladium on carbon (2 mg, 10 wt % on activated carbon, 0.1 wt equiv) sparged under an atmosphere of hydrogen (1 atm) and stirred for 4 hours at ambient temperature. The mixture was sparged under an atmosphere of nitrogen, filtered through a pad of Celite and the filtrate was concentrated in vacuo, providing the titled compound: 1H-NMR (400 MHz, CD3OD) δ 9.07 (1H, s), 8.42 (1H, d, J=7.7 Hz), 7.96 (1H, d, J=8.5 Hz), 7.78-7.68 (2H, m), 7.38-7.37 (2H, m), 7.16-7.11 (2H, m), 5.85 (2H, s), 4.10 (2H, t, J=7.0 Hz), 1.95-1.89 (2H, m), 0.99 (3H, t, J=7.5 Hz), ppm; low resolution mass spectrometry (ES+) m/z 336.0 [(M+H)+; calculated for C20H18FN3O: 336.1].

Workup

  1. customsparged under an atmosphere of hydrogen (1 atm)
  2. customThe mixture was sparged under an atmosphere of nitrogen
  3. filtrationfiltered through a pad of Celite
  4. concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-3e901c97509b4a419a7277d896a4413b
Source dataset
uspto-grants-2014_11
Patent number
US08895580B2

Reaction notes

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