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

HRID 1412559Notes

Reaction equation

HRID 1412559 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-21302480188e4f6a82d39062576b80fa
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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