Potassium Carbonate → Methyl 5-(5,6-dimethoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate

HRID 2391685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2391685
COC1N=C2N=CN(C3SC(C(OC)=O)=C(O)C=3)C2=CC=1OC.[CH3:24][O:25][C:26]1[N:31]=[C:30]2[N:32]([C:35]3[S:39][C:38]([C:40]([O:42][CH3:43])=[O:41])=[C:37]([OH:44])[CH:36]=3)[CH:33]=[N:34][C:29]2=[CH:28][C:27]=1[O:45][CH3:46].C([O-])([O-])=O.[K+].[K+].Br[CH2:54][C:55]1[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=1[C:61]([F:64])([F:63])[F:62]>CN(C)C=O>[CH3:24][O:25][C:26]1[N:31]=[C:30]2[N:32]([C:35]3[S:39][C:38]([C:40]([O:42][CH3:43])=[O:41])=[C:37]([O:44][CH2:54][C:55]4[CH:60]=[CH:59][CH:58]=[CH:57][C:56]=4[C:61]([F:62])([F:63])[F:64])[CH:36]=3)[CH:33]=[N:34][C:29]2=[CH:28][C:27]=1[O:45][CH3:46]

Komponenten

6

Edukt 4

HCID 11430Potassium CarbonateHCID 1230571-(Bromomethyl)-2-(trifluoromethyl)benzeneHCID 68766418methyl 5-(5,6-dimethoxy-1H-imidazo[4,5-b]pyridin-1-yl)-3-hydroxythiophene-2-carboxylateHCID 68767999methyl 5-(5,6-dimethoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-hydroxythiophene-2-carboxylate

Produkt 1

HCID 68766918Methyl 5-(5,6-dimethoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-{[2-(trifluoromethyl)benzyl]oxy}thiophene-2-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of an isomeric mixture of 1.76 g of methyl 5-(5,6-dimethoxy-1H-imidazo[4,5-b]pyridin-1-yl)-3-hydroxythiophene-2-carboxylate and methyl 5-(5,6-dimethoxy-3H-imidazo[4,5-b]pyridin-3-yl)-3-hydroxythiophene-2-carboxylate (example C7) in 20 ml anhydrous N,N-dimethylformamide were added 0.86 g K2CO3 and 1.51 g of 1-(bromomethyl)-2-(trifluoromethyl)benzene under a nitrogen atmosphere. The reaction mixture was stirred for 12 h at room temperature, poured into 200 ml of ice water and stirred for 1 h. The solid was filtered, dissolved in acetonitrile and the isomeric mixture was separated and purified by preparative HPLC to yield compound B4a and compound B4b. The structural assignment of compound B4a was unequivocally established by two-dimensional 1H NMR experiments (NOESY, COSY).

Aufarbeitung

  1. stirringstirred for 1 h
  2. filtrationThe solid was filtered
  3. dissolutiondissolved in acetonitrile
  4. customthe isomeric mixture was separated
  5. custompurified by preparative HPLC
  6. customto yield compound B4a

Quellen und Nachweise

ORD-Eintrag
ord-6bdbb47d9b19414c916ff75f5d4370da
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08273890B2

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