Lithium Chloride → 1H-Indole, 5-ethenyl-1-methyl-

HRID 222477Notes

Reaction equation

[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([C:11]#[C:12][Si](C)(C)C)=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.[Cl-].[Li+].C(C([Sn])=C(CCCC)CCCC)CCC>CN(C=O)C.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([CH:11]=[CH2:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-methyl-5-trimethylsilanylethynyl-1H-indole (0.50 g, 1.95 mmol) in DMF (10 mL) were added lithium chloride (0.32 mg, 7.59 mmol), bis(triphenylphosphine)palladium (II) (0.225 g, 0.195 mmol) and tributylvinyltin (0.80 g, 2.52 mmol). The resulting suspension was heated at 80° C. for 2 h and cooled to room temperature. The reaction mixture was filtered through Celite pad washing with ethyl acetate, organic solvents were evaporated in vacuo. The residue was purified by column chromatography (ethyl acetate:hexane; 5:95) to give a product (290 mg, 94%). 1H NMR (DMSO-d6, 400 MHz) 3.77 (s, 1H), 5.10 (d, J=3.9 Hz, 1H), 5.70 (d, J=7.6 Hz, 1H), 6.40 (d, J=2.5 Hz, 1H), 6.80 (dd, J=11.0, 17.3 Hz, 1H), 7.30-7.41 (m, 3H), 7.58 (s, 1H); 13C NMR (DMSO-d6, 100 MHz) 32.9, 101.1, 110.2, 111.0, 119.2, 119.5, 128.5, 128.8, 130.6, 136.7, 138.3.

Workup

temperaturecooled to room temperature
filtrationThe reaction mixture was filtered through Celite pad
washwashing with ethyl acetate, organic solvents
customwere evaporated in vacuo
customThe residue was purified by column chromatography (ethyl acetate:hexane; 5:95)

Sources & evidence

ORD record: ord-b6b5ba73f8344c1d8b6bcca89a0ece0e
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207216B2

Reaction notes

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