반응 #2018234

ord-bc344503ca5841ccbec0e252d0077c5a

반응 방정식

O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CC(C)(C)OC(=O)/C=C/c1ccn(S(=O)(=O)c2ccc(Br)cc2)c1
(E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester
CC(C)(C)OC(=O)/C=C/c1ccn(S(=O)(=O)c2ccc(Br)cc2)c1
compound D4
CC(C)(C)OC(=O)/C=C/c1ccn(S(=O)(=O)c2ccc(Br)cc2)c1
(E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester
OB(O)c1cccnc1
3-pyridylboronic acid
→
CC(C)(C)OC(=O)/C=C/c1ccn(S(=O)(=O)c2ccc(-c3cccnc3)cc2)c1
title compound
CC(C)(C)OC(=O)/C=C/c1ccn(S(=O)(=O)c2ccc(-c3cccnc3)cc2)c1
(E)-3-[1-(4-Pyridin-3-ylphenylsulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester

반응물

O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
—
aqueous solution
CC(C)(C)OC(=O)/C=C/c1ccn(S(=O)(=O)c2ccc(Br)cc2)c1
(E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester
CC(C)(C)OC(=O)/C=C/c1ccn(S(=O)(=O)c2ccc(Br)cc2)c1
compound D4
CC(C)(C)OC(=O)/C=C/c1ccn(S(=O)(=O)c2ccc(Br)cc2)c1
(E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester
OB(O)c1cccnc1
3-pyridylboronic acid

시약

[Cl][Pd][Cl].c1ccc(P(c2ccccc2)c2ccccc2)cc1
triphenylphosphin palladium (II)-chloride

용매

COCCOC
DME

반응 조건

상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도the mixture is heated
  2. 2
    온도to reflux temperature overnight

실험 절차

0.18 g (E)-3-[1-(4-bromo-benzenesulfonyl)-1H-pyrrol-3-yl]-acrylic acid tert-butyl ester (compound D4) and 62 mg 3-pyridylboronic acid are dissolved in 10 ml DME. A catalytic amount of bis-(triphenylphosphin-palladium (II)-chloride and 0.6 ml of an aqueous solution of sodium carbonate are added and the mixture is heated to reflux temperature overnight. The title compound is isolated by means of chromatography.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08188138B2uspto-grants-2012_05