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Potassium Phosphate, Tribasic → (4-Benzyloxy-6-fluoro-1-methyl-naphthalen-2-yl)-acetic acid methyl ester

HRID 238622
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 238622
[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:23])[CH:11]=2)[C:6]=1Br.[CH3:26]B(O)O.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:1][O:2][C:3](=[O:25])[CH2:4][C:5]1[CH:14]=[C:13]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([F:23])[CH:11]=2)[C:6]=1[CH3:26]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 139377Methylboronic AcidHCID 59326473(4-Benzyloxy-1-bromo-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester

Produkt 1

HCID 59326512(4-Benzyloxy-6-fluoro-1-methyl-naphthalen-2-yl)-acetic acid methyl esterAusbeute 59,5 %

Reagenzien, Katalysatoren, Lösungsmittel

4
HCID 962WaterKatalysatorHCID 167845palladium(II) acetateKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

To a solution of (4-benzyloxy-1-bromo-6-fluoro-naphthalen-2-yl)-acetic acid methyl ester (100 mg, 0.248 mmol, prepared using an analogous procedure to the first step of example 5-1), methylboronic acid (19.3 mg, 0.322 mmol), potassium phosphate (184 mg, 0.868 mmol) and tricyclohexylphosphine (69.4 mg, 0.248 mmol) in toluene (4.0 mL) and water (2 drops) was added palladium acetate (3 mg, 0.0124 mmol) under a nitrogen atmosphere. After being heated under microwave conditions (150° C., 30 minutes), the mixture was cooled to room temperature, then diluted with water (10 mL), and extracted with ethyl acetate (15 mL×2). The combined organic layers were washed with brine (10 mL), dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (10% ethyl acetate in hexanes) to afford (4-benzyloxy-6-fluoro-1-methyl-naphthalen-2-yl)-acetic acid methyl ester (50 mg, 59.5%) as a light yellow solid.

Aufarbeitung

  1. temperaturethe mixture was cooled to room temperature
  2. extractionextracted with ethyl acetate (15 mL×2)
  3. washThe combined organic layers were washed with brine (10 mL)
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (10% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-102f8abdf2484b0f877039ad4dfadf42
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642629B2

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