Ethylene Glycol → HCID 25181650、化合物

HRID 1896024ノート

反応式

HRID 1896024 の反応式
[O-]P([O-])([O-])=O.[K+].[K+].[K+].C(O)CO.I[C:14]1[C:15]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][CH:17]=[CH:18][CH:19]=1.[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH:33]=[C:34]2[CH2:39][CH2:38][NH:37][CH2:36][CH2:35]2)[N:26]=1>C(O)CCC.CCOC(C)=O.[Cu]I>[CH3:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]#[C:32][CH:33]=[C:34]2[CH2:35][CH2:36][N:37]([C:14]3[C:15]([O:20][CH2:21][CH2:22][CH3:23])=[N:16][CH:17]=[CH:18][CH:19]=3)[CH2:38][CH2:39]2)[N:26]=1

参加物

8

反応物 4

HCID 174Ethylene GlycolHCID 62657Potassium Phosphate, TribasicHCID 425531323-Iodo-2-propoxypyridineHCID 875504022-Methyl-6-(3-piperidin-4-ylideneprop-1-ynyl)pyridine

生成物 1

HCID 25181650HCID 25181650、化合物収率 10%

試薬・触媒・溶媒 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 2631-Butanol溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

Into a flamed flask flushed with nitrogen a mixture of CuI (19.4 mg. 0.1 mmol)), K3PO4 (425 mg, 2 mmol), ethylene glycol (112 μL), 3-iodo-2-propoxypyridine (263 mg, 1 mmol) in 1 mL of n-Butanol were added 255 mg of the compound of Example 3 dissolved in 1 mL of n-Butanol. The suspension was heated at 100° C. for 5 h. The reaction mixture was then cooled to r.t., diluted with EtOAc, washed with aq., NaHCO3 and water, dried over Na2SO4 and evaporated to dryness in vacuo. After the work-up the residue was purified by automated flash liquid chromatography (Horizon™-Biotage) eluting with PE-EtOAc 8:2. affording the title product (32 mg, 10%).

後処理

  1. customInto a flamed flask flushed with nitrogen
  2. temperatureThe reaction mixture was then cooled to r.t.
  3. washwashed with aq., NaHCO3 and water
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness in vacuo
  6. customAfter the work-up the residue was purified by automated flash liquid chromatography (Horizon™-Biotage)
  7. washeluting with PE-EtOAc 8:2

出典と根拠

ORDレコード
ord-9487ee5ee34645b489a8be11a9b2cc21
出典データセット
uspto-grants-2013_08
特許番号
US08518916B2

反応ノート

読み込み中…