Potassium Carbonate → 2,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde

HRID 2212606

반응식

HRID 2212606 반응식
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([CH3:21])=[C:9](B3OC(C)(C)C(C)(C)O3)[CH:10]=2)[C:5]([CH3:23])([CH3:22])[CH2:4][C:3]1=[O:24].Br[C:26]1[C:27]([F:37])=[C:28]([CH:31]=[C:32]([F:36])[C:33]=1[O:34][CH3:35])[CH:29]=[O:30].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1.C(O)C.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>[F:37][C:27]1[C:26]([C:9]2[CH:10]=[C:11]3[C:6]([C:5]([CH3:22])([CH3:23])[CH2:4][C:3](=[O:24])[N:2]3[CH3:1])=[CH:7][C:8]=2[CH3:21])=[C:33]([O:34][CH3:35])[C:32]([F:36])=[CH:31][C:28]=1[CH:29]=[O:30]

참가 물질

9

반응물 3

HCID 11430Potassium CarbonateHCID 219664313-Bromo-2,5-difluoro-4-methoxybenzaldehydeHCID 21966467HCID 21966467, 화합물

생성물 1

HCID 219664662,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde

시약·촉매·용매 5

HCID 178418397HCID 178418397, 화합물촉매HCID 702Ethanol용매HCID 962Water용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1,4,4,6-tetramethyl-7-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,4-dihydro-1H-quinoline-2-one (0.36 g, 1.1 mmol), 3-bromo-2,5-difluoro-4-methoxybenzaldehyde (example 13 a) (0.25 g, 0.1 mmol) and potassium carbonate (0.275 g, 1.99 mmol) in toluene (5 mL), ethanol (1 mL) and water (0.75 mL) was degassed with argon for 30 minutes. Tetrakis(triphenylphosphine)palladium(0) (58 mg, 0.05 mmol) was added and the mixture heated at reflux under argon for 20 hrs. 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 purified on silica gel (0%–20% ethyl acetate in hexane) to give 97 mg of 2,5-Difluoro-4-methoxy-3-(1,4,4,6-tetramethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-benzaldehyde.

후처리

  1. customwas degassed with argon for 30 minutes
  2. temperaturethe mixture heated
  3. temperatureat reflux under argon for 20 hrs
  4. washwashed successively with water and brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue was purified on silica gel (0%–20% ethyl acetate in hexane)

출처 및 근거

ORD 기록
ord-d2d5e6a394c041c89ee0859a93a0cc5d
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07102000B2

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