Dichloromethane → 4,4-Dimethyl-6-trimethylsilylethynyl-1,2,3,4-tetrahydroquinoline

HRID 6556

反応式

HRID 6556 の反応式
[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9](Br)[CH:10]=2)[NH:5][CH2:4][CH2:3]1.[CH3:14][Si:15]([C:18]#[CH:19])([CH3:17])[CH3:16].C(Cl)Cl>C(N(CC)CC)C.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1([CH3:13])[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:19]#[C:18][Si:15]([CH3:17])([CH3:16])[CH3:14])[CH:10]=2)[NH:5][CH2:4][CH2:3]1

参加物

6

反応物 3

HCID 6344DichloromethaneHCID 66111TrimethylsilylacetyleneHCID 108239326-Bromo-1,2,3,4-tetrahydro-4,4-dimethylquinoline2 回

生成物 1

HCID 156611344,4-Dimethyl-6-trimethylsilylethynyl-1,2,3,4-tetrahydroquinoline

試薬・触媒・溶媒 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium触媒HCID 8471Triethylamine溶媒

反応条件

温度
50 °C

実験手順

A solution of 1.608 g (6.7 mmol) of 4,4-dimethyl-6-bromo-1,2,3,4-tetrahydroquinoline (Compound 94) in 1.5 ml of triethylamine in a heavy-walled tube was degassed under argon and then treated with 75 mg (0.39 mmol) of cuprous iodide and 150 mg (0.21 mmol) of bis(triphenylphosphine) palladium (II) chloride. The mixture was degassed again under argon, treated with 2.09 g (21.2 mmol) of trimethylsilylacetylene and the tube was sealed. The mixture was heated at 50 degrees C. for 48 h. After cooling to room temperature methylene chloride was added to the reaction mixture and the mixture filtered. The filtrate was concentrated in vacuo and the residue purified by flash chromatography (silica; 10% ethyl acetate in hexanes) to give the title compound as a yellow oil. PMR (CDCl3): δ 0.20 (9H, s), 1.20 (6H, s), 1.57-1.63 (2H, m), 3.16-3.25 (2H, m), 4.02 (1H, broad s), 6.24 (1H, d, J~8.2 Hz), 7.00 (1H, dd, J~8.2 Hz, 1.8 Hz), 7.26 (1H, d, J~1.8 Hz).

後処理

  1. customThe mixture was degassed again under argon
  2. customthe tube was sealed
  3. additionwas added to the reaction mixture
  4. filtrationthe mixture filtered
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthe residue purified by flash chromatography (silica; 10% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-093606782439496bbfe40e499def95b8
出典データセット
uspto-grants-1993_09
特許番号
US05248777

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