Triethylamine → HCID 53882369、化合物

HRID 651654ノート

反応式

HRID 651654 の反応式
I[C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[CH:4][N:3]=1.[C:9]([O:13][C:14](=[O:25])[NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]#[CH:23])[C:17]1=[O:24])([CH3:12])([CH3:11])[CH3:10].C(N(CC)CC)C>C(#N)C.O.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[C:9]([O:13][C:14](=[O:25])[NH:15][C@H:16]1[CH2:20][CH2:19][N:18]([CH2:21][C:22]2[O:8][C:7]3[C:2](=[N:3][CH:4]=[CH:5][CH:6]=3)[CH:23]=2)[C:17]1=[O:24])([CH3:12])([CH3:10])[CH3:11]

参加物

9

反応物 3

HCID 8471TriethylamineHCID 971792-Iodopyridin-3-olHCID 53895069HCID 53895069、化合物

生成物 1

HCID 53882369HCID 53882369、化合物

試薬・触媒・溶媒 5

HCID 83717Copper iodide触媒HCID 178418476HCID 178418476、化合物触媒HCID 962Water溶媒HCID 6342Acetonitrile溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

A mixture of 2-iodo-3-hydroxy-pyridine (0.44 g, 2 mmol), (2-oxo-1-prop-2-ynyl-pyrrolidin-3-(S)-yl)-carbamic acid tert-butyl ester (0.6 g, 2.5 mmol), bis(triphenylphosphine)-palladium(II) chloride (Pd(PPh3)2Cl2) (50 mg), copper iodide (25 mg) and triethylamine (3 mL) in 3 mL of acetonitrile is heated in a sealed tube at 120° C. for 2 hours. After cooling, the reaction mixture is diluted with water and EtOAc and the layers are separated. The aqueous layer is extracted with EtOAc. The combined organic layers are washed with water and saturated NaCl solution, then dried over MgSO4, filtered and concentrated. The crude product is purified by column chromatography eluting with a gradient of 25% EtOAc/CH2Cl2 to 90% EtOAc/CFH2Cl2 to yield the title compound as a white solid.

後処理

  1. temperatureAfter cooling
  2. customthe layers are separated
  3. extractionThe aqueous layer is extracted with EtOAc
  4. washThe combined organic layers are washed with water and saturated NaCl solution
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude product is purified by column chromatography
  9. washeluting with a gradient of 25% EtOAc/CH2Cl2 to 90% EtOAc/CFH2Cl2

出典と根拠

ORDレコード
ord-ebd828c7abbd4b2ba7ac10700b1e7e27
出典データセット
uspto-grants-2001_08
特許番号
US06281227B1

反応ノート

読み込み中…