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

HRID 1916738

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-8d9cc0d65ae3403d809b0469febe7095
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08618132B2

Linked notes

Loading…