Triethylamine → HCID 18931451, compound

HRID 1598974Notes

Reaction equation

[CH3:1][C:2]1([CH3:28])[C:11]2[C:6](=[CH:7][C:8](OS(C(F)(F)F)(=O)=O)=[CH:9][CH:10]=2)[N:5]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:4](=[O:27])[CH2:3]1.C(N(CC)CC)C.[CH3:36][Si:37]([C:40]#[CH:41])([CH3:39])[CH3:38]>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(Cl)Cl>[CH3:1][C:2]1([CH3:28])[C:11]2[C:6](=[CH:7][C:8]([C:41]#[C:40][Si:37]([CH3:39])([CH3:38])[CH3:36])=[CH:9][CH:10]=2)[N:5]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=2)[C:4](=[O:27])[CH2:3]1

Participants

Conditions

Temperature: 85 °C

Procedure

To a solution of 0.20 g (0.57 mmol) of 4,4-dimethyl-3,4-dihydro-N-(4-methylphenyl)-7-[(trifluoromethanesulfonyl)oxy]-2(1H)-quinolinone (Compound 18) in 1.45 g (2.0 mL, 14 mmol) of triethylamine were added 0.70 g (1.0 mL, 7.1 mmol) of (trimethylsilyl)acetylene and 94 mg (0.13 mmol) of bis(triphenylphosphine)palladium(II) chloride. The resulting mixture was heated at 85° C. for 16 h. The reaction mixture was cooled, methylene chloride was added and the mixture adsorbed onto silica gel. The mixture was purified by flash chromatography (25% ethyl acetate in hexanes) to give the title compound as a foam. PNMR (300 MHz, CDCl3) d 0.19 (9 H, s), 1.40 (6 H, s), 2.44 (3 H, s), 2.66 (2 H, s), 6.53 (1 H, d, J=1.4 Hz), 7.09 (2 H, d, J=8.4 Hz), 7.15 (1 H, dd, J=7.9, 1.4 Hz), 7.25 (1 H, d, J=7.9 Hz), 7.33 (2 H, d, J=8.4 Hz).

Workup

temperatureThe reaction mixture was cooled
customThe mixture was purified by flash chromatography (25% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-e0284192d6fa4e33b835b69fea87ba38
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739338

Reaction notes

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