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Ethyl Acetate → 7-(5-Chloro-2-methoxyphenyl)-8-methoxycarbonyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

HRID 871972
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HRID 871972 반응식
Br[C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]2[C:5]([NH:6][C:7]([CH3:19])([CH3:18])[C:8](=[O:17])[N:9]2[CH3:16])=[CH:4][CH:3]=1.[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([O:30][CH3:31])=[C:25](B(O)O)[CH:26]=1.C(=O)([O-])[O-].C(OCC)(=O)C>CN(C)C=O.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.O.C(OCC)C>[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([O:30][CH3:31])=[C:23]([C:2]2[C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]3[C:5]([NH:6][C:7]([CH3:19])([CH3:18])[C:8](=[O:17])[N:9]3[CH3:16])=[CH:4][CH:3]=2)[CH:22]=1
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참가 물질

9

반응물 4

HCID 8857Ethyl AcetateHCID 19660Carbonate IonHCID 27357515-Chloro-2-methoxyphenylboronic acidHCID 247809997-Bromo-8-methoxycarbonyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one

생성물 1

HCID 247809987-(5-Chloro-2-methoxyphenyl)-8-methoxycarbonyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one수율 86%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

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온도
80 °C

실험 절차

A mixture of 7-bromo-8-methoxycarbonyl-1,3,3-trimethyl-3,4-dihydro-1H-quinoxalin-2-one (Reference Compound No. 9, 3.75 g, 11.5 mmol), 5-chloro-2-methoxyphenylboronic acid (2.57 g, 13.8 mmol), cessium carbonate (7.49 g, 23.0 mmol) and tetrakis(triphenylphosphine)palladium (0) (1.33 g, 1.16 mmol) was suspended in anhydrous N,N-dimethylformamide (70 ml) and stirred at 80° C. overnight under argon atmosphere. After cooling down, ethyl acetate (300 mL), diethylether (150 mL) and water (400 mL) were added and partitioned. The organic layer was washed with water (250 mL) and saturated brine (150 mL) successively, dried over anhydrous magnesium sulfate, and then the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled reference compound (3.84 g) as a colorless amorphous product. (Yield 86%)

후처리

  1. temperatureAfter cooling down
  2. custompartitioned
  3. washThe organic layer was washed with water (250 mL) and saturated brine (150 mL) successively
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate)

출처 및 근거

ORD 기록
ord-d4c9c12995e14589bca3bf7b504f3b1d
출처 데이터셋
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08975256B2

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