Sodium Carbonate → 4-(3-(2-Furan-3-yl-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol

HRID 383284ノート

反応式

HRID 383284 の反応式
Cl[C:2]1[CH:7]=[C:6]([C:8]2[N:12]3[CH: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+]>C(O)C.O>[O:25]1[CH:29]=[CH:28][C:27]([C:2]2[CH:7]=[C:6]([C:8]3[N:12]4[CH: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

6

反応物 3

HCID 10340Sodium CarbonateHCID 2734358Furan-3-boronic acidHCID 252619024-[3-(2-Chloro-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-ylamino]-cyclohexanol

生成物 1

HCID 252617524-(3-(2-Furan-3-yl-pyridin-4-yl)-imidazo[1,2-a]pyridin-6-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)-imidazo[1,2-a]pyridin-6-ylamino]-cyclohexanol (Example 2.1) (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 ethanol (2 ml) and H2O (0.7 ml), under inert atmosphere 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% methanol 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% methanol in EtOAc

出典と根拠

ORDレコード
ord-738fb88aff4346eeaf6fd6ad508623b4
出典データセット
uspto-grants-2013_02
特許番号
US08367662B2

反応ノート

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