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

HRID 530008

Reaktionsgleichung

Reaktionsgleichung von HRID 530008
[C:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([C:17]2[CH:22]=[CH:21][C:20]([NH:23]C3C=CC(C)=CC=3C(O)=O)=[C:19]([O:34][CH3:35])[CH:18]=2)=[CH:13][C:12]=1[O:36][CH3:37])([OH:3])=[O:2].[CH3:38]OC1C=C(C2C=CC(N)=C(OC)C=2)C=CC=1N.IC1C=CC=CC=1C(O)=O.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>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]([C:14]2[CH:15]=[CH:16][C:11]([NH:10][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[C:1]([O:3][CH3:38])=[O:2])=[C:12]([O:36][CH3:37])[CH:13]=2)=[CH:18][C:19]=1[O:34][CH3:35]

Komponenten

7

Edukt 4

HCID 69412-Iodobenzoic acidHCID 8411DianisidineHCID 10796Cesium carbonateHCID 575198362-((4'-((2-carboxyphenyl)amino)-3,3'-dimethoxy-[1,1'-biphenyl]-4-Yl)amino)-5-methylbenzoic acid

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 synthesixed 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-5c23d420c62045e68db9a3d4808304ec
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09351971B2

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