Pyridine → 1-benzyl-N-[4-(1-methylethoxy)phenyl]-1H-pyrazol-5-amine

HRID 519846Notes

Reaction equation

HRID 519846 reaction equation
[CH2:1]([N:8]1[C:12]([NH2:13])=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([C:17]1[CH:22]=[CH:21][C:20]([O:23]B(O)O)=[CH:19][CH:18]=1)(C)C.N1C=C[CH:30]=[CH:29][CH:28]=1>O1CCCC1.C(OCC)(=O)C.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH2:1]([N:8]1[C:12]([NH:13][C:17]2[CH:18]=[CH:19][C:20]([O:23][CH:29]([CH3:30])[CH3:28])=[CH:21][CH:22]=2)=[CH:11][CH:10]=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 3

HCID 1049PyridineHCID 770611-Benzyl-1H-pyrazol-5-amineHCID 537142394-Isopropylphenylboric acid

Product 1

HCID 670098001-benzyl-N-[4-(1-methylethoxy)phenyl]-1H-pyrazol-5-amineYield 26%

Reagents, catalysts & solvents 3

HCID 8895Cupric acetateCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 1-benzyl-1H-pyrazol-5-amine (1.7 g), 4-isopropylphenylboric acid (2.0 g), copper acetate (1.8 g), pyridine (4.0 mL) and molecular sieves 4A (4 g) in tetrahydrofuran (50 mL) was stirred for 15 hr. The reaction mixture was diluted with ethyl acetate, the insoluble material was filtered off through celite, and the filtrate was concentrated. The residue was purified by silica gel column chromatography to give the title compound as a pale-yellow amorphous solid (0.80 g, 26%).

Workup

  1. filtrationthe insoluble material was filtered off through celite
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-deda8624a5784d5390a48c0e24de33b2
Source dataset
uspto-grants-2015_08
Patent number
US09115136B2

Reaction notes

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