Water → 3-(1,4-Diisopropyl-6-methyl-1,2,3,4-tetrahydro-7-quinoxalinyl)-4-methoxybenzaldehyde

HRID 488819

반응식

HRID 488819 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([N:6]([CH:15]([CH3:17])[CH3:16])[CH2:7][CH2:8][N:9]2[CH:12]([CH3:14])[CH3:13])=[CH:4][C:3]=1[CH3:18].[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH:27]=[O:28])=[CH:23][C:22]=1B(O)O.C(=O)([O-])[O-].[K+].[K+].O>COCCOC.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:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH3:18])=[C:2]([C:22]3[CH:23]=[C:24]([CH:25]=[CH:26][C:21]=3[O:20][CH3:19])[CH:27]=[O:28])[CH:11]=2)[N:6]([CH:15]([CH3:17])[CH3:16])[CH2:7][CH2:8]1)([CH3:14])[CH3:13]

참가 물질

7

반응물 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343675-Formyl-2-methoxyphenylboronic acidHCID 22268301HCID 22268301, 화합물

생성물 1

HCID 222683433-(1,4-Diisopropyl-6-methyl-1,2,3,4-tetrahydro-7-quinoxalinyl)-4-methoxybenzaldehyde

시약·촉매·용매 2

HCID 178418397HCID 178418397, 화합물촉매HCID 80711,2-Dimethoxyethane용매

실험 절차

A mixture of 7-bromo-1,4-diisopropyl-6-methyl-1,2,3,4-tetrahydroquinoxaline (469 mg, 1.51 mmol), 2-methoxy-5-formylphenylboronic acid (407 mg, 2.26 mmol), potassium carbonate (834 mg, 6.03 mmol) and water (2.5 mL) in anhydrous 1,2-dimethoxyethane (30 mL) was degassed with argon for 15 minutes prior to the addition of tetrakis(triphenylphosphine)palladium (0) (349 mg, 0.30 mmol). The reaction mixture was heated under reflux for 8.5 hours, allowed to cool to room temperature and extracted with ethyl acetate (2×100 mL). The organic extracts were successively washed with water (100 mL), saturated aqueous NH4Cl (100 mL), saturated aqueous NaCl (100 mL), dried over MgSO4 and filtered. Removal of the solvent under reduced pressure gave an oil which was purified by column chromatography, using a Biotage 40S cartridge, eluting with 10% ethyl acetate/90% hexane. The title compound was isolated as bright yellow solid (315 mg, 57%).

후처리

  1. customwas degassed with argon for 15 minutes
  2. temperatureThe reaction mixture was heated
  3. temperatureunder reflux for 8.5 hours
  4. extractionextracted with ethyl acetate (2×100 mL)
  5. washThe organic extracts were successively washed with water (100 mL), saturated aqueous NH4Cl (100 mL), saturated aqueous NaCl (100 mL)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customRemoval of the solvent under reduced pressure
  9. customgave an oil which
  10. customwas purified by column chromatography
  11. washeluting with 10% ethyl acetate/90% hexane

출처 및 근거

ORD 기록
ord-8c7b368876644e1d9de9d4b20aac2b9d
출처 데이터셋
uspto-grants-2005_12
특허 번호
US06974826B2

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