Reaction #1099052

ord-9b5c0dac91ee436c9b208f39c20e1b07

Reaction equation

O=P([O-])([O-])[O-].[K+].[K+].[K+]
K3PO4
Cc1nn(-c2cccc(Br)c2)c(C)c1C(=O)O
1-(3-bromo-phenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid
OB(O)/C=C/c1ccc(Cl)cc1
trans-2-(4-chlorophenyl)vinylboronic acid
→
Cc1nn(-c2cccc(/C=C/c3ccc(Cl)cc3)c2)c(C)c1C(=O)O
1-{3-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenyl}-3,5-dimethyl-1H-pyrazole-4-carboxylic acid
Yield 63.0%

Reactants

O=P([O-])([O-])[O-].[K+].[K+].[K+]
K3PO4
Cc1nn(-c2cccc(Br)c2)c(C)c1C(=O)O
1-(3-bromo-phenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid
OB(O)/C=C/c1ccc(Cl)cc1
trans-2-(4-chlorophenyl)vinylboronic acid

Reagents

None

Solvents

ClCCl
CH2Cl2

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Othergave
  2. 2
    Filtrationfiltration the title compound in 63% yield as light yellow solid

Procedure

In analogy to the procedure described in Example 14C], but with 2.8 eq of K3PO4, 1-(3-bromo-phenyl)-3,5-dimethyl-1H-pyrazole-4-carboxylic acid and trans-2-(4-chlorophenyl)vinylboronic acid gave after suspending in CH2Cl2 and filtration the title compound in 63% yield as light yellow solid. MS: 352.2 (M+, 1 Cl).

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07977358B2uspto-grants-2011_07