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

HRID 1916737

反応式

HRID 1916737 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 962Water溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-ce09a9c6faef40be990a975c27380976
出典データセット
uspto-grants-2013_12
特許番号
US08618132B2

関連ノート

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