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

HRID 6556

반응식

HRID 6556 반응식
[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

참가 물질

6

반응물 3

HCID 6344DichloromethaneHCID 66111TrimethylsilylacetyleneHCID 108239326-Bromo-1,2,3,4-tetrahydro-4,4-dimethylquinoline2회

생성물 1

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

시약·촉매·용매 2

HCID 6102075Dichlorobis(triphenylphosphine)palladium촉매HCID 8471Triethylamine용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-093606782439496bbfe40e499def95b8
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05248777

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