1,2-Dimethoxyethane → 3-(1-Isopropyl-7-methyl-1,2,3,4-tetrahydro-6-quinolinyl)-4-methoxybenzaldehyde

HRID 1884496노트

반응식

HRID 1884496 반응식
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[CH3:12])[N:8]([CH:13]([CH3:15])[CH3:14])[CH2:7][CH2:6][CH2:5]2.[C:16](=[O:19])([O-])[O-].[K+].[K+].CO[CH2:24][CH2:25][O:26][CH3:27]>O.C(OCC)(=O)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH:13]([N:8]1[C:9]2[C:4](=[CH:3][C:2]([C:3]3[CH:2]=[C:11]([CH:10]=[CH:24][C:25]=3[O:26][CH3:27])[CH:16]=[O:19])=[C:11]([CH3:12])[CH:10]=2)[CH2:5][CH2:6][CH2:7]1)([CH3:15])[CH3:14]

참가 물질

7

반응물 3

HCID 80711,2-DimethoxyethaneHCID 11430Potassium CarbonateHCID 222683656-Bromo-1-isopropyl-7-methyl-1,2,3,4-tetrahydro-quinoline

생성물 1

HCID 222682923-(1-Isopropyl-7-methyl-1,2,3,4-tetrahydro-6-quinolinyl)-4-methoxybenzaldehyde수율 79%

시약·촉매·용매 3

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 6-bromo-1-isopropyl-7-methyl-1,2,3,4-tetrahydro-quinoline (0.85 g, 3.16 mmol), 2-methoxy-5-formyl boronic acid (1.13 g, 6.31 mmol) and potassium carbonate (1.70 g, 12.64 mmol) in 1,2-dimethoxyethane (30 mL) and water (1.5 mL) was degassed with argon for 15 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.80 g, 0.63 mmol) was added and the mixture heated at reflux under argon for 35 hours. The solution was cooled to room temperature, diluted with ethyl acetate and washed successively with water and brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The residue was chromatographed and silica gel (eluent: ethyl acetate/hexane, 1:9) to give 0.81 g of 3-(1-isopropyl-7-methyl-1,2,3,4-tetrahydro-6-quinolinyl)-4-methoxybenzaldehyde (79%). 1H NMR (500 MHz; CDCl3): δ1.18 (s, 3 H); 1.20 (s, 3 H); 1.94 (m, 2 H); 2.06 (s, 3 H); 2.72 (m, 2 H); 3.18 (m, 2 H); 3.85 (s, 3 H); 4.16 (m, 1 H); 6.57 (s, 1 H); 6.78 (s, 1 H); 7.02 (d, 1 H); 7.69 (d, 1 H); 7.34 (s, 1 H); 7.84 (m, 1 H); 9.89 (s, 1 H).

후처리

  1. customwas degassed with argon for 15 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon for 35 hours
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was chromatographed

출처 및 근거

ORD 기록
ord-f9c92c14a4ec4c4b8fa5f20523e59a26
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06765013B2

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