Tetrahydrofuran → ethyl 3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-5-trimethylsilanylethynyl-1H-indole-2-carboxylate

HRID 1916737

반응식

HRID 1916737 반응식
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[C:5]2[CH3:16].[C:17]([Si:19]([CH3:22])([CH3:21])[CH3:20])#[CH:18].[NH:23]1[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]1.[CH2:29]1COCC1>O.[Cu]I>[CH3:16][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([C:18]#[C:17][Si:19]([CH3:22])([CH3:21])[CH3:20])[CH:3]=2)[N:7]([CH2:27][CH2:28][N:23]2[CH2:24][CH2:25][CH2:26][CH2:29]2)[C:6]=1[C:11]([O:13][CH2:14][CH3:15])=[O:12]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 8082PiperidineHCID 66111TrimethylsilylacetyleneHCID 616662Ethyl 5-bromo-3-methyl-1H-indole-2-carboxylate

생성물 1

HCID 69075563ethyl 3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-5-trimethylsilanylethynyl-1H-indole-2-carboxylate

시약·촉매·용매 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

Under an argon atmosphere 577 mg (0.5 mmol) tetrakis-triphenylphosphane-palladium and 95 mg (0.5 mmol) CuI are added to a solution of 2.82 g (10 mmol) ethyl 5-bromo-3-methyl-1H-indole-2-carboxylate and 1.52 mL (11 mmol) ethynyl-trimethyl-silane in 3 mL (30 mmol) piperidine and 30 mL THF and the reaction mixture is stirred for 14 h at 60° C. It is diluted with water, extracted exhaustively with EtOAc, the combined organic phases are washed with saturated NaCl solution and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, cyc/EtOAc 9:1).

후처리

  1. extractionextracted exhaustively with EtOAc
  2. washthe combined organic phases are washed with saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customis purified by chromatography (silica gel, cyc/EtOAc 9:1)

출처 및 근거

ORD 기록
ord-ce09a9c6faef40be990a975c27380976
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618132B2

연결된 노트

불러오는 중…