Hydrochloric Acid → ethyl 5-ethynyl-3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-1H-indole-2-carboxylate

HRID 271734

Reaction equation

ClCCN1CCCC1.Cl.[CH3:10][C:11]1[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([C:20]#[C:21][Si](C)(C)C)[CH:18]=2)[N:13]([CH2:26][CH2:27][N:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:12]=1[C:33]([O:35][CH2:36][CH3:37])=[O:34].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O>[C:20]([C:17]1[CH:18]=[C:19]2[C:14](=[CH:15][CH:16]=1)[N:13]([CH2:26][CH2:27][N:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1)[C:12]([C:33]([O:35][CH2:36][CH3:37])=[O:34])=[C:11]2[CH3:10])#[CH:21]

Participants

Conditions

Temperature: 60 °C

Procedure

Under an argon atmosphere 562 mg (3.3 mmol) 1-(2-chloro-ethyl)-pyrrolidine (used as the hydrochloride) are added to a suspension of 900 mg (3.0 mmol) ethyl 3-methyl-1-(2-pyrrolidin-1-yl-ethyl)-5-trimethylsilanylethynyl-1H-indole-2-carboxylate and 457 mg (3.3 mmol) K2CO3 in 10 mL DMF and the reaction mixture is stirred for 42 h at 60° C. It is diluted with water, extracted exhaustively with EtOAc, the combined organic phases are washed with water and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:1).

Workup

extractionextracted exhaustively with EtOAc
washthe combined organic phases are washed with water
dry with materialdried over Na2SO4
customis purified by chromatography (silica gel, EtOAc/MeOH/NH3 90:10:1)

Sources & evidence

ORD record: ord-a828ffcc3fa44e938eace57f9a6f232d
Source dataset: uspto-grants-2008_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07452911B2

Linked notes

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