Ethylene Glycol → 4-(3-Bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol

HRID 383283ノート

反応式

HRID 383283 の反応式
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[Br:9][C:10]1[N:14]2[CH:15]=[C:16](I)[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1.C(O)CO.[NH2:24][C@H:25]1[CH2:30][CH2:29][C@H:28]([OH:31])[CH2:27][CH2:26]1>C(O)(C)C.[Cu]I>[Br:9][C:10]1[N:14]2[CH:15]=[C:16]([NH:24][CH:25]3[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]3)[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1

参加物

7

反応物 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 684848303-Bromo-6-iodoimidazo[1,2-A]pyridine2 回HCID 178511715HCID 178511715、化合物

生成物 1

HCID 684826874-(3-Bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 3776Isopropanol溶媒

反応条件

温度
80 °C

実験手順

Copper (I) iodide (0.1 eq, 1.45 g, 7.68 mmol) and potassium phosphate tribasic (2 eq, 0.153 mol, 32.5 g) are stirred at RT under an atmosphere of argon during the addition of 3-bromo-6-iodo-imidazo[1,2-a]pyridine (Intermediate F) (25 g, 77 mmol, 1 eq) in isopropyl alcohol (200 ml), ethylene glycol (2 eq, 0.153 mol, 8.5 ml) and finally trans-4-aminocyclohexanol (2 eq, 17.5 g, 153 mmol) The reaction is heated at 80° C. for 40 hours. The majority of the solvent is removed in vacuo and the residue is diluted with water (500 ml) and extracted with EtOAc (3×500 ml). The combined organic portions are dried (MgSO4) and concentrated in vacuo. Purification by flash chromatography on silica eluting with 0-15% MeOH in EtOAc gives 4-(3-bromo-imidazo[1,2-a]pyridin-6-ylamino)-cyclohexanol; [M+H]+=310 (312)

後処理

  1. customThe majority of the solvent is removed in vacuo
  2. additionthe residue is diluted with water (500 ml)
  3. extractionextracted with EtOAc (3×500 ml)
  4. dry with materialThe combined organic portions are dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica eluting with 0-15% MeOH in EtOAc

出典と根拠

ORDレコード
ord-1d3cc9f3195149cf8d2fb6bce46ba202
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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