Triethylamine → 6-[6-[(trimethylsilanyl)ethynyl]-pyridin-3-yl]-pyrido[2',1':2,3]-imidazo[4,5-c]isoquinolin-5(6H)-one

HRID 1670694노트

반응식

HRID 1670694 반응식
C(N(CC)CC)C.[CH3:8][Si:9]([C:12]#[CH:13])([CH3:11])[CH3:10].Br[C:15]1[N:20]=[CH:19][C:18]([N:21]2[C:30]3[N:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]4=[N:33][C:29]=3[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:38])=[CH:17][CH:16]=1>CN(C=O)C.[Cu]I.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>[CH3:8][Si:9]([C:12]#[C:13][C:15]1[N:20]=[CH:19][C:18]([N:21]2[C:30]3[N:31]4[CH:37]=[CH:36][CH:35]=[CH:34][C:32]4=[N:33][C:29]=3[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]2=[O:38])=[CH:17][CH:16]=1)([CH3:11])[CH3:10]

참가 물질

7

반응물 3

HCID 8471TriethylamineHCID 66111TrimethylsilylacetyleneHCID 247710936-(6-bromo-pyridin-3-yl)-pyrido-[2',1':2,3]imidazo[4,5-c]isoquinolin-5(6H)-one

생성물 1

HCID 577670226-[6-[(trimethylsilanyl)ethynyl]-pyridin-3-yl]-pyrido[2',1':2,3]-imidazo[4,5-c]isoquinolin-5(6H)-one수율 96%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매2회HCID 178418476HCID 178418476, 화합물촉매2회HCID 6228Dimethylformamide용매

실험 절차

CuI (0.2 equiv., 0.256 mmol, 0.049 g), dichlorobis(triphenylphosphine)-palladium(II) (0.1 equiv., 0.13 mmol, 0.090 g), triethylamine (1.0 equiv., 1.28 mmol, 0.129 g), (trimethylsilyl)acetylene (10.0 equiv., 12.8 mmol, 1.26 g) and KI (10.0 equiv., 12.8 mmol, 2.12 g) were added to a mixture of 6-(6-bromo-pyridin-3-yl)-pyrido-[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one (21) (1.0 equiv., 1.28 mmol, 0.50 g) in dry DMF (10 ml). The reaction mixture was stirred at room temperature under N2 atmosphere for 24 h. After addition of a second portion of CuI (0.20 equiv., 0.256 mmol, 0.049 g) and dichlorobis(triphenylphosphine)-palladium(II) (0.1 equiv., 0.13 mmol, 0.090 g), the reaction mixture was further stirred at 60° C. for 17 h. The solvent was evaporated under reduced pressure and the pasty residue was mixed with dichloromethane and washed with water. The organic layer was evaporated under reduced pressure and the residue purified by column chromatography (ethyl acetate/heptane 60:40) to afford 6-[6-[(trimethylsilanyl)ethynyl]-pyridin-3-yl]-pyrido[2′,1′:2,3]-imidazo[4,5-c]isoquinolin-5(6H)-one (I9) (0.50 g, yield=96%, purity (LC)=95%).

후처리

  1. stirringthe reaction mixture was further stirred at 60° C. for 17 h
  2. customThe solvent was evaporated under reduced pressure
  3. additionthe pasty residue was mixed with dichloromethane
  4. washwashed with water
  5. customThe organic layer was evaporated under reduced pressure
  6. customthe residue purified by column chromatography (ethyl acetate/heptane 60:40)

출처 및 근거

ORD 기록
ord-c774a75f6db64060bee37906934b4d3f
출처 데이터셋
uspto-grants-2011_08
특허 번호
US07994187B2

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