Trimethylsilylacetylene → 1-Methyl-5-trimethylsilanylethynyl-1H-indole

HRID 222476

Reaction equation

I[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([CH3:11])[CH:6]=[CH:5]2.[C:12]([Si:14]([CH3:17])([CH3:16])[CH3:15])#[CH:13]>N1CCCC1>[CH3:11][N:7]1[C:8]2[C:4](=[CH:3][C:2]([C:13]#[C:12][Si:14]([CH3:17])([CH3:16])[CH3:15])=[CH:10][CH:9]=2)[CH:5]=[CH:6]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 5-iodo-1-methyl-1H-indole (200 mg, 0.778 mmol) in pyrrolidine (5 mL) was added ethynyl-trimethyl-silane (92 mg, 0.932 mmol), followed by tetrakis-triphenyl-phosphine palladium (61 mg, 0.233 mmol) after which the reaction mixture was heated at 50° C. for 12 h. The reaction mixture was filtered and the filtrate evaporated in vacuo to obtain a residue, which was purified by column chromatography (ethyl acetate:hexane; 5:95) to give a product (150 g, 84%). 1H NMR (CDCl3, 400 MHz) 0.25 (s, 9H), 3.76 (s, 3H), 6.44 (d, J=3.0 Hz, 1H), 7.04 (d, J=3.0 Hz, 1H), 7.23 (d, J=8.4 Hz, 1H), 7.30 (dd, J=1.4 Hz, 1H), 7.78 (d, J=1.4 Hz, 1H); 13C NMR (CDCl3, 100 MHz) 0.18, 32.8, 90.9, 101.2, 107.0, 109.0, 113.6, 125.3, 125.4, 128.1, 129.6, 136.4.

Workup

filtrationThe reaction mixture was filtered
customthe filtrate evaporated in vacuo
customto obtain a residue, which
customwas purified by column chromatography (ethyl acetate:hexane; 5:95)

Sources & evidence

ORD record: ord-5f53458e1c2e44e08097bb9e3561dbbe
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207216B2

Linked notes

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