Reaktion #9244

ord-60da8dac3f014ed1b9238d03474e7f55

Reaktionsgleichung

CCNC(=O)Nc1nc2ccc(Br)cc2s1
1-(6-bromo-2-benzothiazolyl)-3-ethylurea
OB(O)Oc1ccc(Cl)cc1
4-chlorophenylboric acid
O=C([O-])O.[Na+]
sodium bicarbonate
→
CCNC(=O)Nc1nc2ccc(-c3ccc(Cl)cc3)cc2s1
desired compound
Ausbeute 18.0%
CCNC(=O)Nc1nc2ccc(-c3ccc(Cl)cc3)cc2s1
1-(6-(4-Chlorophenyl)-2-benzothiazolyl)-3-ethylurea
Ausbeute 18.0%

Edukte

—
1-(6-(4-pyrrazolyl)-2-benzothiazolyl)-3-ethylurea
CCNC(=O)Nc1nc2ccc(Br)cc2s1
1-(6-bromo-2-benzothiazolyl)-3-ethylurea
OB(O)Oc1ccc(Cl)cc1
4-chlorophenylboric acid
O=C([O-])O.[Na+]
sodium bicarbonate

Reagenzien

c1ccc([P](c2ccccc2)(c2ccccc2)[Pd]([P](c2ccccc2)(c2ccccc2)c2ccccc2)([P](c2ccccc2)(c2ccccc2)c2ccccc2)[P](c2ccccc2)(c2ccccc2)c2ccccc2)cc1
Pd(PPh3)4

Lösungsmittel

CN(C)C=O.O
DMF water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewas reacted

Vorschrift

Similar to the synthesis of 1-(6-(4-pyrrazolyl)-2-benzothiazolyl)-3-ethylurea, a mixture of 1-(6-bromo-2-benzothiazolyl)-3-ethylurea, 4-chlorophenylboric acid, sodium bicarbonate, and Pd(PPh3)4 in DMF/water mixed solvent (5/1) was reacted to give the desired compound 0.020 g (18%). LC/MS 330 (M−1); LC retention time 2.70 min.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US07091227B2uspto-grants-2006_08