Dimethylformamide → HCID 18931449, compound

HRID 1598975Notes

Reaction equation

[CH3:1][C:2]1([CH3:22])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[CH:13])=[CH:9][CH:10]=2)[N:5]([C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][CH:15]=2)[C:4](=[O:21])[CH2:3]1.I[C:24]1[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=1.C(N(CC)CC)C.CN(C)C=O>[Cu]I.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([CH3:22])[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][C:24]3[CH:34]=[CH:33][C:27]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:26][CH:25]=3)=[CH:9][CH:10]=2)[N:5]([C:14]2[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][CH:19]=2)[C:4](=[O:21])[CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a mixture of 0.13 g (0.45 mmol) of 4,4-dimethyl-3,4-dihydro-N-(4-methylphenyl)-7-ethynyl-2(1H)-quinolinone (Compound 20) and 0.29 g (1.0 mmol) of ethyl 4-iodobenzoate were added 2.9 g (4.0 mL, 29 mmol) of triethylamine, 2.0 mL of dimethylformamide, 0.019 g (0.10 mmol) of copper(I)iodide, and 0.067 g (0.10 mmol) of bis(triphenylphosphine)palladium(II) chloride, consecutively. The resulting mixture was heated at 50° C. for 16 hours. Thereafter methylene chloride was added and the reaction mixture was adsorbed onto silica gel. The mixture was purified by flash chromatography (15% ethyl acetate in hexanes) to give the title compound as an orange solid. PNMR (300 MHz, CDCl3) d 1.41 (3 H, t, J=7.1 Hz), 1.43 (6 H, s), 1.86 (2 H, t, J=6.0 Hz), 2.44 (3 H, s), 2.48 (2 H, s), 4.37 (2 H, q, J=7.1 Hz), 6.59 (1 H, d, J=1.5 Hz), 7.12 (2 H, d, J=8.3 Hz), 7.20-7.38 (4 H, m), 7.50 (2 H, d, J=8.1 Hz), 7.98 (2 H, d, J=8.1 Hz).

Workup

customThe mixture was purified by flash chromatography (15% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-c199af032fd74e01832b33e180d03db5
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739338

Reaction notes

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