Potassium Iodide → 4-{4-[2-(2-Butylpyridinylamino)ethoxy]phenyl}butanoic acid

HRID 1881033ノート

反応式

HRID 1881033 の反応式
CO[C:3](=O)[CH2:4][CH2:5][CH2:6]C1C=CC(OCCBr)=CC=1.C(N[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][N:24]=1)CCC.[I-].[K+].C[O:32][C:33](=[O:57])[CH2:34][CH2:35][CH2:36][C:37]1[CH:42]=[CH:41][C:40]([O:43][CH2:44][CH2:45][N:46](C(CC)C)C2C=CC=CN=2)=[CH:39][CH:38]=1.[OH-].[Na+]>O1CCCC1.CO.C(OCC)(=O)C.C(N(CC)CC)C>[CH2:3]([C:23]1[C:28]([NH:46][CH2:45][CH2:44][O:43][C:40]2[CH:39]=[CH:38][C:37]([CH2:36][CH2:35][CH2:34][C:33]([OH:57])=[O:32])=[CH:42][CH:41]=2)=[CH:27][CH:26]=[CH:25][N:24]=1)[CH2:4][CH2:5][CH3:6]

参加物

10

反応物 5

HCID 4875Potassium IodideHCID 14798Sodium HydroxideHCID 14322668N-Butyl-2-pyridinamine2 回HCID 251578524-(4-(2-Bromoethoxy)phenyl)butanoic acid methyl esterHCID 672995864-{4-[2-(2-Butyl(pyridin-2-yl)amino)ethoxy]phenyl}butanoic acid methyl ester

生成物 1

HCID 672998564-{4-[2-(2-Butylpyridinylamino)ethoxy]phenyl}butanoic acid収率 11%

試薬・触媒・溶媒 4

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒2 回HCID 8471Triethylamine溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-(4-(2-bromoethoxy)phenyl)butanoic acid methyl ester (3) (956 mg) from Step 3, and N-butylpyridine-2-amine (4) (1.4 g) from Step 4, were dissolved in tetrahydrofuran (6 mL), then triethylamine (0.88 mL) and potassium iodide (530 mg) were added, and refluxed overnight by heating. Ethyl acetate (100 mL) was added to the reaction solution, and the organic layer was washed with water (100 mL) and saturated sodium chloride solution (50 mL). After drying on anhydrous sodium sulfate, filtration and vacuum concentration, the residue was purified by silica gel flash column chromatography (developing solvent: n-hexane:ethyl acetate=6:1) to give a mixture of 4-{4-[2-(2-butyl(pyridin-2-yl)amino)ethoxy]phenyl}butanoic acid methyl ester and N-butylpyridine-2-amine (4). This mixture was dissolved in methanol (4 mL) and tetrahydrofuran (4 mL), 2N sodium hydroxide aqueous solution (1 mL) was added, then stirred overnight at room temperature. The reaction solution was concentrated with 2N hydrochloric acid (1.1 mL), then the residue was purified by silica gel flash column chromatography (developing solvent: n-hexane:ethyl acetate=1:1) to give the above-identified compound (128 mg, yield 11%) as a colorless oil.

後処理

  1. temperaturerefluxed overnight
  2. temperatureby heating
  3. washthe organic layer was washed with water (100 mL) and saturated sodium chloride solution (50 mL)
  4. dry with materialAfter drying on anhydrous sodium sulfate, filtration and vacuum concentration
  5. customthe residue was purified by silica gel flash column chromatography (developing solvent: n-hexane:ethyl acetate=6:1)
  6. customto give
  7. concentrationThe reaction solution was concentrated with 2N hydrochloric acid (1.1 mL)
  8. customthe residue was purified by silica gel flash column chromatography (developing solvent: n-hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-b21391d705584a27b351a315529ba71c
出典データセット
uspto-grants-2012_11
特許番号
US08318781B2

反応ノート

読み込み中…