Nitrogen → 4-[3-(2-furan-3-yl-pyridin-4-yl)-3H-imidazo[4,5-b]pyridin-5-ylamino]-cyclohexanol

HRID 1524193ノート

反応式

HRID 1524193 の反応式
Cl[C:2]1[CH:7]=[C:6]([N:8]2[C:12]3=[N:13][C:14]([NH:17][CH:18]4[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]4)=[CH:15][CH:16]=[C:11]3[N:10]=[CH:9]2)[CH:5]=[CH:4][N:3]=1.[O:25]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26]1.C([O-])([O-])=O.[Na+].[Na+].N#N>CCO.O>[O:25]1[CH:29]=[CH:28][C:27]([C:2]2[CH:7]=[C:6]([N:8]3[C:12]4=[N:13][C:14]([NH:17][CH:18]5[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20][CH2:19]5)=[CH:15][CH:16]=[C:11]4[N:10]=[CH:9]3)[CH:5]=[CH:4][N:3]=2)=[CH:26]1

参加物

7

反応物 4

HCID 947NitrogenHCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 866518694-[3-(2-Chloro-pyridin-4-yl)-3H-imidazo[4,5-b]pyridine-5-ylamino]-cyclohexanol

生成物 1

HCID 444760434-[3-(2-furan-3-yl-pyridin-4-yl)-3H-imidazo[4,5-b]pyridin-5-ylamino]-cyclohexanol

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒2 回

実験手順

To 4-[3-(2-Chloro-pyridin-4-yl)-3H-imidazo[4,5-b]pyridine-5-ylamino]-cyclohexanol (1 eq, 100 mg, 0.29 mmol), 3-furyl boronic acid (1.05 eq, 0.3 mmol, 34 mg), Na2CO3 (2 eq, 0.58 mmol, 62 mg) in EtOH (2 ml) and H2O (0.7 ml) under inert atmosphere of N2 is added tetakis(triphenylphosphine) palladium (0.1 eq, 0.029 mmol, 21 mg). The reaction is heated in using microwave radiation at 80° C. for 2 hours. The mixture is diluted with H2O (5 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by flash chromatography on silica eluting with 0-2.5% MeOH in EtOAc to afford the title compound; [M+H]+ 375.

後処理

  1. temperatureThe reaction is heated
  2. customat 80° C.
  3. customfor 2 hours
  4. extractionextracted with EtOAc
  5. washThe combined organic portions are washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified by flash chromatography on silica eluting with 0-2.5% MeOH in EtOAc

出典と根拠

ORDレコード
ord-847662492943457f8fb85cbc5723f9ba
出典データセット
uspto-grants-2015_07
特許番号
US09079897B2

反応ノート

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