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

HRID 2391685노트

반응식

HRID 2391685 반응식
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]

참가 물질

6

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-6bdbb47d9b19414c916ff75f5d4370da
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273890B2

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