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

HRID 2391685ノート

反応式

HRID 2391685 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6bdbb47d9b19414c916ff75f5d4370da
出典データセット
uspto-grants-2012_09
特許番号
US08273890B2

反応ノート

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