Chloride → HCID 18931458, compound

HRID 1598964Notes

Reaction equation

[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8](Br)=[CH:9][CH:10]=2)[N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.[CH3:27][Si:28]([C:31]#[CH:32])([CH3:30])[CH3:29].[Cl-]>[Cu]I.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.C(Cl)Cl>[CH3:1][C:2]1([CH3:19])[C:11]2[C:6](=[CH:7][C:8]([C:32]#[C:31][Si:28]([CH3:30])([CH3:29])[CH3:27])=[CH:9][CH:10]=2)[N:5]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH2:4][CH2:3]1

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 0.10 g (0.32 mmol) of 4,4-dimethyl-1,2,3,4-tetrahydro-N-phenyl-7-bromoquinoline (Compound 6) and 5.0 g (4.0 mL, 36 mmol) triethylamine were added 0.032 g (0.17 mmol) of copper(I) iodide, 0.70 g (1.0 mL, 7.1 mmol) of (trimethylsilyl)acetylene, and 0.050 g (0.07 mmol) of bis(triphenylphosphine)palladium(ID chloride. The resulting mixture was heated at 70° C. for 22 hours. The reaction was cooled, methylene chloride was added, and the mixture was adsorbed onto silica gel. The mixture was purified by flash chromatography (hexanes) to give the title compound as a yellow solid. PNMR (300 MHz, CDCl3) d 0.17 (9 H, s), 1.32 (6 H, s), 1.82 (2 H, t, J=6.0 Hz), 3.61 (2 H, t, J=6.0 Hz), 6.85 (2 H, overlapping d's), 7.15-7.41 (6 H, m).

Workup

temperatureThe reaction was cooled
customThe mixture was purified by flash chromatography (hexanes)

Sources & evidence

ORD record: ord-66a7a5c6776c462585ffc4d19fa01955
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05739338

Reaction notes

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