Hydrochloric Acid → HCID 136377240, Verbindung

HRID 919913Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919913
[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:24])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9](Br)=[CH:8]2)=[O:4].[N:25]1[O:29][N:28]=[C:27]2[CH:30]=[C:31](B(O)O)[CH:32]=[CH:33][C:26]=12.[O-]P([O-])([O-])=O.[K+].[K+].[K+].O.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.Cl>C1(C)C=CC=CC=1.[Cl-].[Na+].O.CC([O-])=O.CC([O-])=O.[Pd+2].CCOC(C)=O>[CH3:1][O:2][C:3]([C:5]1[C:6]([OH:24])=[C:7]2[C:12](=[CH:13][N:14]=1)[N:11]([CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)[C:10](=[O:22])[C:9]([C:31]1[CH:32]=[CH:33][C:26]3[C:27]([CH:30]=1)=[N:28][O:29][N:25]=3)=[CH:8]2)=[O:4]

Komponenten

11

Edukt 6

HCID 313Hydrochloric AcidHCID 962WaterHCID 62657Potassium Phosphate, TribasicHCID 4672597Benzo[C][1,2,5]Oxadiazole-5-Boronic AcidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 682974771-Benzyl-3-bromo-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester

Produkt 1

HCID 136377240HCID 136377240, VerbindungAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 167845palladium(II) acetateKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 1-benzyl-3-bromo-5-hydroxy-2-oxo-1,2-dihydro-[1,7]naphthyridine-6-carboxylic acid methyl ester (80 mg, 0.21 mmol), benzo[1,2,5]oxadiazole-5-boronic acid (51 mg, 0.31 mmol), K3PO4 (87 mg, 0.41 mmol), H2O (7.4 mg, 0.41 mmol), SPhos (4.2 mg, 0.010 mmol) and Pd(OAc)2 (4.2 mg, 0.0062 mmol) in toluene (5 mL) was heated at 100° C. under nitrogen atmosphere for 16 h. After the mixture was cooled to r.t., brine and EtOAc were added. 1 M HCl was added with stirring until pH was about 3, and the organic layer was dried over MgSO4 and concentrated. The crude product was first purified by silica gel chromatography (0-60% EtOAc/hexanes+1% AcOH), then by preparative TLC (20% EtOAc/CH2Cl2) to give 33 mg of the title compound. MS: (+) m/z 429.27 (M+1).

Aufarbeitung

  1. temperatureAfter the mixture was cooled to r.t.
  2. dry with materialthe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe crude product was first purified by silica gel chromatography (0-60% EtOAc/hexanes+1% AcOH)

Quellen und Nachweise

ORD-Eintrag
ord-b8ab95a9b5004163b191976db4a9fab9
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09271970B2

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