Water → 1-(Tert-butoxycarbonyl)-5-(3-dimethylamino-2-propyn-1-yl)indole

HRID 20991

Reaction equation

[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13](I)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:18][N:19]([CH3:23])[CH2:20][C:21]#[CH:22].O>C(NCC)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([CH2:22][C:21]#[C:20][N:19]([CH3:23])[CH3:18])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

Conditions

Temperature: 80 °C

Procedure

1-(tert-Butoxycarbonyl)-5-iodoindole (1.00 g, 2.91 mmol) was dissolved in diethylamine (20 mL), and the solution was added with bis(triphenylphosphine)dichloropalladium (163 mg, 0.233 mmol), cuprous iodide (44.4 mg, 0.233 mmol) and 1-dimethylamino-2-propyne (0.628 mL, 5.82 mmol), followed by stirring at 80° C. for 7.0 hours. The reaction mixture was added with water and extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by preparative thin-layer chromatography (chloroform/methanol=19/1) to obtain 1-(tert-butoxycarbonyl)-5-(3-dimethylamino-2-propyn-1-yl)indole (0.78 g, yield 90%).

Workup

extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried over anhydrous sodium sulfate
customThe solvent was evaporated under reduced pressure
customThe residue was purified by preparative thin-layer chromatography (chloroform/methanol=19/1)

Sources & evidence

ORD record: ord-a8a7964606714175a8ec31928416e35e
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745641B2

Linked notes

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