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Toluene → 3-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-methoxy-benzaldehyde

HRID 883065
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HRID 883065 반응식
Br[C:2]1[CH:11]=[C:10]2[C:5]([C:6]([CH3:16])([CH3:15])[CH2:7][C:8](=[O:14])[N:9]2[CH2:12][CH3:13])=[CH:4][C:3]=1[CH3:17].[CH3:18][O:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]=[O:27])=[CH:22][C:21]=1B(O)O.C1(C)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>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.C(O)C>[CH2:12]([N:9]1[C:10]2[C:5](=[CH:4][C:3]([CH3:17])=[C:2]([C:21]3[CH:22]=[C:23]([CH:24]=[CH:25][C:20]=3[O:19][CH3:18])[CH:26]=[O:27])[CH:11]=2)[C:6]([CH3:16])([CH3:15])[CH2:7][C:8]1=[O:14])[CH3:13]
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참가 물질

7

반응물 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 27343675-Formyl-2-methoxyphenylboronic acidHCID 219664867-Bromo-1-ethyl-4,4,6-trimethyl-3,4-dihydro-1H-quinolin-2-one

생성물 1

HCID 866117603-(1-Ethyl-4,4,6-trimethyl-2-oxo-1,2,3,4-tetrahydro-quinolin-7-yl)-4-methoxy-benzaldehyde수율 99%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

A round bottom flask was charged with 6.0 g of Compound 1A (20.3 mmol), 5.5 g of 2-methoxy-5-formylphenylboronic acid (30.4 mmol) and tetrakis(triphenylphosphine)palladium(0), (1.17 g, 0.10 mmol). The flask was sealed and 100 mL of toluene and 30 mL of ethanol was added. The resulting solution was stirred to dissolve the reactants and then 21 mL of 2M K2CO3 was added via syringe. The reaction mixture was heated to 80° C. for 4 hours. After cooling, the reaction mixture was partitioned between ethyl acetate (200 mL) and water (75 mL). The water layer was further extracted (2×100 mL) and the combined organic layers were washed with water (50 mL) followed by brine (50 mL), dried over magnesium sulfate, filtered and excess solvent removed on the rotary evaporator. The crude product was purified by flash chromatography (EtOAc/Hexanes; gradient 20% to 40%) to give 7.05 g (99%) of product Compound 1B as a foamy solid. MS (electrospray): mass calculated for C22H25NO3, 351.18; m/z found 352.4, [M+H]+. 1HNMR (300 MHz, CDCl3): 9.94 (s, 1H), 7.93 (dd, J=2.1, 8.6 Hz, 1H), 7.73 (d, J=2.1 Hz, 1H), 7.18 (s, 1H), 7.12 (d, J=8.6 Hz, 1H), 6.85 (s, 1H), 4.01 (q, J=7.1 Hz, 2H), 3.90 (s, 3H), 2.52 (s, 2H), 2.10 (s, 3H), 1.33 (s, 6H), 1.23 (t, J=6.9 Hz, 3H).

후처리

  1. customThe flask was sealed
  2. dissolutionto dissolve the reactants
  3. temperatureAfter cooling
  4. customthe reaction mixture was partitioned between ethyl acetate (200 mL) and water (75 mL)
  5. extractionThe water layer was further extracted (2×100 mL)
  6. washthe combined organic layers were washed with water (50 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customexcess solvent removed on the rotary evaporator
  10. customThe crude product was purified by flash chromatography (EtOAc/Hexanes; gradient 20% to 40%)

출처 및 근거

ORD 기록
ord-4139f958283449d78e2cc2ae61bf97b8
출처 데이터셋
uspto-grants-2012_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08236819B2

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