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

HRID 1916737

Reaction equation

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]

Participants

Conditions

Temperature: 60 °C

Procedure

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).

Workup

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

Sources & evidence

ORD record: ord-ce09a9c6faef40be990a975c27380976
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Linked notes

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