Potassium Carbonate → 5-Chloro-N-((1-(4-(2,4-dimethoxypyrimidin-5-yl)phenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide

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Reaktionsgleichung

[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19](I)=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1.[CH3:23][O:24][C:25]1[N:30]=[C:29]([O:31][CH3:32])[C:28](B(O)O)=[CH:27][N:26]=1.C([O-])([O-])=O.[K+].[K+]>C(#N)C.O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][C:11]2[N:12]=[N:13][N:14]([C:16]3[CH:21]=[CH:20][C:19]([C:28]4[C:29]([O:31][CH3:32])=[N:30][C:25]([O:24][CH3:23])=[N:26][CH:27]=4)=[CH:18][CH:17]=3)[CH:15]=2)=[O:8])=[CH:4][CH:3]=1

Komponenten

Reaktionsbedingungen

Temperatur: 125 °C

Versuchsvorschrift

The mixture of 5-chloro-N-((1-(4-iodophenyl)-1H-1,2,3-triazol-4-yl)methyl)thiophene-2-carboxamide (4.1, 48 mg, 0.11 mmol, synthesized by procedures similar to those that were used to make compound 1.5 described in SCHEME 1), 2,4-dimethoxypyrimidin-5-ylboronic acid (4.2, 24 mg, 0.13 mmol), PdCl2(PPh3)2 (38 mg, 0.05 mmol), K2CO3 (23 mg, 0.16 mmol) in 1 mL acetonitrile and 1 mL water was degassed using argon stream and heated in microwave reactor at 125° C. for 15 min. The mixture was filtered and directly subjected to reverse phase prep HPLC to isolate the title compound. MS found for C20H17ClN6O3S (M+H)+ 457.1, 459.1 (Cl pattern).

Aufarbeitung

customsynthesized by procedures similar to those that
customwas degassed
filtrationThe mixture was filtered

Quellen und Nachweise

ORD-Eintrag: ord-4f70147975714e1fbcb6d2f849feffd0
Quelldatensatz: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07696352B2

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