Toluene → HCID 22344624, Verbindung

HRID 2299803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2299803
Cl[C:2]1[N:7]2[CH:8]=[C:9]([CH2:11][O:12][C:13]3[CH:34]=[CH:33][C:16]([CH2:17][O:18]/[N:19]=[C:20](/[C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)\[CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:15][CH:14]=3)[N:10]=[C:6]2[CH:5]=[CH:4][CH:3]=1.[C:35]1(B(O)O)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1.C(=O)(O)[O-].[Na+].C1(C)C=CC=CC=1>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(OCC)(=O)C.CCCCCC.CO.O>[C:35]1([C:2]2[N:7]3[CH:8]=[C:9]([CH2:11][O:12][C:13]4[CH:34]=[CH:33][C:16]([CH2:17][O:18]/[N:19]=[C:20](/[C:27]5[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=5)\[CH2:21][CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:15][CH:14]=4)[N:10]=[C:6]3[CH:5]=[CH:4][CH:3]=2)[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Komponenten

9

Edukt 4

HCID 1140TolueneHCID 66827Phenylboronic AcidHCID 516892Sodium BicarbonateHCID 22344575HCID 22344575, Verbindung

Produkt 1

HCID 22344624HCID 22344624, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittelHCID 21226206Ethyl acetate hexaneLösungsmittel

Versuchsvorschrift

A mixture of methyl E-4-[4-(5-chloroimidazo[1,2-a]pyridin-2-ylmethoxy)benzyloxyimino]-4-phenylbutyrate (550 mg), phenylboronic acid (168 mg), sodium bicarbonate (348 mg), toluene (20 ml), water (2 ml) and methanol (2 ml) was stirred at room temperature for 30 minutes under argon atmosphere. To this was added tetrakis(triphenylphosphine)palladium (0) (80 mg) and heated to reflux for 36 hours. The reaction mixture was cooled to room temperature, the organic layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain methyl E-4-[4-(5-phenylimidazo[1,2-a]pyridin-2-ylmethoxy)benzyloxyimino]-4-phenylbutyrate (490 mg, yield 82%) as a colorless oil from an ethyl acetate-hexane (3:2, v/v)-eluted fraction.

Aufarbeitung

  1. temperatureheated
  2. temperatureto reflux for 36 hours
  3. temperatureThe reaction mixture was cooled to room temperature
  4. washthe organic layer was washed with an aqueous saturated solution of sodium chloride
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-90abc20c95264336b09055bdd8759a6a
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06495581B1

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