2-Aminophenylboronic acid hydrochloride → HCID 66958336, compound

HRID 1360574Notes

Reaction equation

HRID 1360574 reaction equation
[CH2:1]([N:5]1[C:9]([CH2:10][C:11]([OH:14])([CH3:13])[CH3:12])=[C:8](Br)[C:7]([C:16]#[N:17])=[N:6]1)[CH2:2][CH2:3][CH3:4].Cl.[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1B(O)O>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[NH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:8]1[C:7]([C:16]#[N:17])=[N:6][N:5]([CH2:1][CH2:2][CH2:3][CH3:4])[C:9]=1[CH2:10][C:11]([OH:14])([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 164270902-Aminophenylboronic acid hydrochlorideHCID 66959135HCID 66959135, compound

Product 1

HCID 66958336HCID 66958336, compound

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

A modification of the method described in Part H of Example 1255 was used to treat 1-butyl-4-bromo-5-(2-hydroxy-2-methylpropyl)-1H-pyrazole-3-carbonitrile (2.7 g, 9.2 mmol). Two equivalents of 2-aminophenylboronic acid hydrochloride (3.2 g, 18.4 mmol) and 2 mol % dichlorobis(triphenylphosphine)palladium(II) (0.126 g, 0.18 mmol) were added at the beginning of the reaction, and the reaction was heated at reflux for five hours. The crude product was purified by chromatography on a HORIZON HPFC system (40+M cartridge, eluting with 0 to 50% ethyl acetate in hexanes to provide 4-(2-aminophenyl)-1-butyl-5-(2-hydroxy-2-methylpropyl)-1H-pyrazole-3-carbonitrile.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for five hours
  3. customThe crude product was purified by chromatography on a HORIZON HPFC system (40+M cartridge
  4. washeluting with 0 to 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-16a6a613b86c47208e5638e650711cba
Source dataset
uspto-grants-2011_02
Patent number
US07879849B2

Reaction notes

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