Tetrahydrofuran → 1-(2-Fluoro-4-hydroxyphenyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 2089972Notes

Reaction equation

HRID 2089972 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[CH:20]=[C:19]([O:21][CH3:22])[C:18](=[O:23])[C:17]([C:24]3[N:28]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[N:27]=[CH:26][CH:25]=3)=[N:16]2)=[C:11]([F:35])[CH:10]=1)C1C=CC=CC=1.C1COCC1>[Pd].CO>[F:35][C:11]1[CH:10]=[C:9]([OH:8])[CH:14]=[CH:13][C:12]=1[N:15]1[CH:20]=[C:19]([O:21][CH3:22])[C:18](=[O:23])[C:17]([C:24]2[N:28]([C:29]3[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=3)[N:27]=[CH:26][CH:25]=2)=[N:16]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 58072350HCID 58072350, compound

Product 1

HCID 594362421-(2-Fluoro-4-hydroxyphenyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-oneYield 91.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 1-[4-(benzyloxy)-2-fluorophenyl]-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (5.53 g, 11.8 mmol), 10% Pd—C (50% wet, 3.0 g), THF (150 mL), and MeOH (150 mL) was hydrogenated for 1.5 h at room temperature. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was recrystallized from MeOH/H2O to give the title compound (4.07 g, 91% yield) as a pale yellow solid: mp 223-224° C.; NMR (300 MHz, DMSO-d6): δ ppm 3.75 (3H, s), 6.60 (1H, ddd, J=1.1, 2.6, 8.7 Hz), 6.73 (1H, dd, J=2.6, 12.8 Hz), 6.90-6.96 (2H, m), 7.28-7.44 (5H, m), 7.78 (1H, d, J=1.9 Hz), 8.39 (1H, d, J=1.9 Hz), 10.44 (1H, brs). LC-MS (ESI) m/z 379 [M+H]+. Anal. Calcd for C20H15FN4O3.0.5H2O: C, 62.01; H, 4.16; N, 14.46. Found: C, 62.18; H, 4.16; N, 14.49.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was recrystallized from MeOH/H2O

Sources & evidence

ORD record
ord-9e6b7bbcac7145ddb917f079af000c2a
Source dataset
uspto-grants-2013_05
Patent number
US08435995B2

Reaction notes

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