2-Iodobenzoic acid → Methyl 2-((4'-amino-3,3'-dimethoxy-[1,1'-biphenyl]-4-yl)amino)benzoate

HRID 876751

Reaktionsgleichung

Reaktionsgleichung von HRID 876751
[CH2:1]1CCC(N2CCN(C(C3C=CC=CC=3)CC3C=CC=CC=3)CC2)CCC1.[CH3:28][O:29][C:30]1[CH:31]=[C:32]([C:37]2[CH:42]=[CH:41][C:40]([NH2:43])=[C:39]([O:44][CH3:45])[CH:38]=2)[CH:33]=[CH:34][C:35]=1[NH2:36].I[C:47]1[CH:55]=[CH:54][CH:53]=[CH:52][C:48]=1[C:49]([OH:51])=[O:50].C([O-])([O-])=O.[Cs+].[Cs+]>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1C=CC(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[NH2:36][C:35]1[CH:34]=[CH:33][C:32]([C:37]2[CH:42]=[CH:41][C:40]([NH:43][C:47]3[CH:55]=[CH:54][CH:53]=[CH:52][C:48]=3[C:49]([O:51][CH3:1])=[O:50])=[C:39]([O:44][CH3:45])[CH:38]=2)=[CH:31][C:30]=1[O:29][CH3:28]

Komponenten

7

Edukt 4

HCID 69412-Iodobenzoic acidHCID 8411DianisidineHCID 10796Cesium carbonateHCID 12263803Piperazine, 1-cycloheptyl-4-(1,2-diphenylethyl)-

Produkt 1

HCID 57519834Methyl 2-((4'-amino-3,3'-dimethoxy-[1,1'-biphenyl]-4-yl)amino)benzoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 86670201Pd2(dba)3 DPPPKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Compound Ic-7 can be synthesized by reacting commercially available 3,3′-dimethoxy-[1,1′-biphenyl]-4,4′-diamine (1 equivalent) with 1.2 equivalents of the commercially available methyl ester of iodobenzoic acid in the presence of Pd2(dba)3/DPPP (0.1-0.5 equiv) and 1.2 equivalents Cs2CO3 in toluene at 110° C. for 20 h with vigorous stirring. The intermediate compound methyl 2-((4′-amino-3,3′-dimethoxy-[1,1′-biphenyl]-4-yl)amino)benzoate is isolated by flash chromatography on a C18 column. The product is then reacted by addition of 1.2 equivalent of methyl 2-iodo-5-methylbenzoate in the presence of catalytic (0.1-0.5 equiv) Pd2(dba)3/DPPP and 1.2 equivalents anhydrous, finely powdered Cs2CO3 in toluene at 110° C. for 20 h to yield methyl 2-((3,3′-dimethoxy-4′-((2-(methoxycarbonyl)phenyl)amino)-[1,1′-biphenyl]-4-yl)amino)-5-methylbenzoate. The methyl esters can then be hydrolyzed under basic conditions followed by acidification to yield compound Ic-7,2-((4′-((2-carboxyphenyl)amino)-3,3′-dimethoxy-[1,1′-biphenyl]-4-yl)amino)-5-methylbenzoic acid.

Aufarbeitung

  1. customat 110° C.
  2. customfor 20 h

Quellen und Nachweise

ORD-Eintrag
ord-b4ca2ac33f294431ada39abbbb1ffc24
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987271B2

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