Triethylamine → HCID 53882369, 화합물

HRID 651654노트

반응식

HRID 651654 반응식
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]

참가 물질

9

반응물 3

HCID 8471TriethylamineHCID 971792-Iodopyridin-3-olHCID 53895069HCID 53895069, 화합물

생성물 1

HCID 53882369HCID 53882369, 화합물

시약·촉매·용매 5

HCID 83717Copper iodide촉매HCID 178418476HCID 178418476, 화합물촉매HCID 962Water용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
120 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-ebd828c7abbd4b2ba7ac10700b1e7e27
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281227B1

반응 노트

불러오는 중…