Reaction #1099095

ord-b99934ea4b5441f5a70d604f654bd869

Reaction equation

O=P([O-])([O-])[O-].[K+].[K+].[K+]
K3PO4
CCN(CC)C1CCN(C(=O)c2nn(C)c(-c3cccc(Br)c3)c2C)C1
[5-(3-bromo-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone
OB(O)/C=C/c1ccc(Cl)cc1
trans-2-(4-chlorophenyl)vinylboronic acid
→
CCN(CC)C1CCN(C(=O)c2nn(C)c(-c3cccc(C=Cc4ccc(Cl)cc4)c3)c2C)C1
(5-{3-[2-(4-chloro-phenyl)-vinyl]-phenyl}-1,4-dimethyl-1H-pyrazol-3-yl)-(3-diethylamino-pyrrolidin-1-yl)-methanone
Yield 67.0%

Reactants

O=P([O-])([O-])[O-].[K+].[K+].[K+]
K3PO4
CCN(CC)C1CCN(C(=O)c2nn(C)c(-c3cccc(Br)c3)c2C)C1
[5-(3-bromo-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone
OB(O)/C=C/c1ccc(Cl)cc1
trans-2-(4-chlorophenyl)vinylboronic acid

Reagents

None

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Procedure

In analogy to the procedure described in example 14C] but with 2.8 eq of K3PO4, [5-(3-bromo-phenyl)-1,4-dimethyl-1H-pyrazol-3-yl]-(3-diethylamino-pyrrolidin-1-yl)-methanone and trans-2-(4-chlorophenyl)vinylboronic acid gave (5-{3-[2-(4-chloro-phenyl)-vinyl]-phenyl}-1,4-dimethyl-1H-pyrazol-3-yl)-(3-diethylamino-pyrrolidin-1-yl)-methanone in 67% yield as light brown oil. MS: 477.0 (MH+, 1 Cl).

Source

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