Ethyl Acetate → 4-[1-methyl-4-(4-pyridinyl)-1H-pyrazol-3-yl]Phenol

HRID 33842Notes

Reaction equation

HRID 33842 reaction equation
C([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:19]([C:20]3[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=3)=[CH:18][N:17]([CH3:26])[N:16]=2)=[CH:11][CH:10]=1)C1C=CC=CC=1.C(OCC)(=O)C>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:26][N:17]1[CH:18]=[C:19]([C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)[C:15]([C:12]2[CH:13]=[CH:14][C:9]([OH:8])=[CH:10][CH:11]=2)=[N:16]1

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 442349314-[3-(4-Benzyloxy-phenyl)-1-methyl-1H-pyrazol-4-yl]-pyridine

Product 1

HCID 1359152134-[1-methyl-4-(4-pyridinyl)-1H-pyrazol-3-yl]PhenolYield 91.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-[3-(4-Benzyloxy-phenyl)-1-methyl-1H-pyrazol-4-yl]-pyridine (1.28 g) in ethanol (50 ml)/ethyl acetate (50 ml) in a parr bottle was added Palladium hydroxide (500 mg). The parr bottle was charged to 40 psi on a shaker for 6 h. The reaction mixture was filtered and concentrated. MPLC biotage chromatography eluting with methanol (1-7%)/chloroform provided the title compound (860 mg, 91%). 1H NMR (400 MHz, DMSO) δ 9.53 (s, 1H), 8.39 (d, J=5.8 Hz, 2 H), 7.15 (m, 4H), 6.72 (d, J=8.7 Hz, 1H), 3.84 (s, 3H); MS: (M+H m/z=252.2).

Workup

  1. additionThe parr bottle was charged to 40 psi on a shaker for 6 h
  2. filtrationThe reaction mixture was filtered
  3. concentrationconcentrated
  4. washMPLC biotage chromatography eluting with methanol (1-7%)/chloroform

Sources & evidence

ORD record
ord-d4fd34a2745b4481b3a507dcf0d1ea92
Source dataset
uspto-grants-2008_09
Patent number
US07429665B2

Reaction notes

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