Reaktion #9243

ord-a5f3ce06d6ac4f33ac47c498605c9889

Reaktionsgleichung

CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1
1-(6-(3-aminophenyl)-2-benzothiazolyl)-3-ethylurea
CCNC(=O)Nc1nc2ccc(Br)cc2s1
1-(6-bromo-2-benzothiazolyl)-3-ethylurea
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CN(C)C=O.O
DMF water
→
CCNC(=O)Nc1nc2ccc(-c3cn[nH]c3)cc2s1
desired compound
Ausbeute 30.0%
CCNC(=O)Nc1nc2ccc(-c3cn[nH]c3)cc2s1
1-(6-(4-Pyrazolyl)-2-benzothiazolyl)-3-ethylurea
Ausbeute 30.0%

Edukte

CCNC(=O)Nc1nc2ccc(-c3cccc(N)c3)cc2s1
1-(6-(3-aminophenyl)-2-benzothiazolyl)-3-ethylurea
CCNC(=O)Nc1nc2ccc(Br)cc2s1
1-(6-bromo-2-benzothiazolyl)-3-ethylurea
O=C([O-])[O-].[Na+].[Na+]
sodium carbonate
CN(C)C=O.O
DMF water

Reagenzien

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

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigewas reacted

Vorschrift

Similar to the synthesis of 1-(6-(3-aminophenyl)-2-benzothiazolyl)-3-ethylurea, a mixture of 4-pyrazolylboronic pinacolate, 1-(6-bromo-2-benzothiazolyl)-3-ethylurea, sodium carbonate, and Pd(PPh3)4 in DMF/water mixed solvent was reacted to give the desired compound 0.543 g (30%). LC/MS 288.2 (M+1); LC retention time 2.61 min.

Quelle

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