Tetrahydrofuran → Methyl 2-amino-5-methoxy-3-methylbenzoate

HRID 249919

Reaktionsgleichung

Reaktionsgleichung von HRID 249919
[NH2:1][C:2]1C(OC)=CC(Br)=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].CB(O)O.[F-].[K+].[C:21]([PH+](C(C)(C)C)C(C)(C)C)(C)(C)C.[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[NH2:1][C:2]1[C:35]([CH3:21])=[CH:34][C:38]([O:37][CH3:36])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Komponenten

7

Edukt 5

HCID 8028TetrahydrofuranHCID 139377Methylboronic AcidHCID 522689Potassium FluorideHCID 4060964Tri-t-butylphosphoniumHCID 13894022Methyl 2-amino-5-bromo-3-methoxybenzoate

Produkt 1

HCID 20281873Methyl 2-amino-5-methoxy-3-methylbenzoateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

A mixture of methyl 2-amino-5-bromo-3-methoxybenzoate (6.50 g, 25 mmol), methylboronic acid (3.0 g, 50 mmol), potassium fluoride (5.8 g, 100 mmol) and tri-t-butylphosphonium tetrafluoroborte (0.87 g, 3.0 mmol) in THF (200 mL) was deoxygenated and then backfilled with argon. Tris(dibenzylideneacetone)dipalladium(0) (1.43 g, 1.5 mmol), was added and the mixture was heated at 70° C. for 17 h under an argon atmosphere. The reaction mixture was concentrated and the residue purified by column chromatography (silica gel, 0% to 5% EtOAc in hexanes) to afford methyl 2-amino-5-methoxy-3-methylbenzoate (3.55 g, 73%) 1H NMR consistent.

Aufarbeitung

  1. customwas deoxygenated
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue purified by column chromatography (silica gel, 0% to 5% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-35df134f9a174ac298eb7dd43559fd3c
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07863271B2

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