Potassium Carbonate → HCID 57779630, Verbindung

HRID 509178

Reaktionsgleichung

Reaktionsgleichung von HRID 509178
Br[C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[OH:9])=[CH:4][CH:3]=1.[F:16][C:17]1[CH:22]=[CH:21][C:20](B(O)O)=[CH:19][CH:18]=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>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.COCCOC>[F:16][C:17]1[CH:22]=[CH:21][C:20]([C:2]2[CH:7]=[CH:6][C:5]([CH:8]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)[OH:9])=[CH:4][CH:3]=2)=[CH:19][CH:18]=1

Komponenten

8

Edukt 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 98221p-Bromobenzhydryl alcoholHCID 2856454-Fluorophenylboronic acid

Produkt 1

HCID 57779630HCID 57779630, VerbindungAusbeute 57 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel2×HCID 80711,2-DimethoxyethaneLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of 11 (1 g, 3.80 mmol) and 4-fluorophenyl boronic acid (585 mg, 4.18 mmol) in a 2:1 mixture of DME:water (30 mL), was added Pd(PPh3)4 (307 mg, 0.27 mmol), tri-o-toly phosphine (81 mg, 0.27 mmol) and potassium carbonate (2.63 g, 19.0 mmol). The solution was heated to 80° C. and stirred for 16 hours. Then water (50 mL) was added and the organic residue was extracted with ethyl acetate (2×40 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The residue was purified via prep-HPLC (ISCO) in silica gel column with a gradient of ethyl acetate (2-50%) in hexane to afford compound 12 as a white solid (600 mg, 57%). 1H NMR (DMSO-d6) δ (ppm): 7.67-7.63 (m, 2H), 7.56 (d, J=8.4 Hz, 2H), 7.45-7.38 (m, 4H), 7.32-7.17 (m, 5H), 5.93 (d, J=3.9 Hz, 1H), 5.73 (d, J=3.8 Hz, 1H).

Aufarbeitung

  1. extractionthe organic residue was extracted with ethyl acetate (2×40 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified via prep-HPLC (ISCO) in silica gel column with a gradient of ethyl acetate (2-50%) in hexane

Quellen und Nachweise

ORD-Eintrag
ord-da5a203b464143d0b413389485d66857
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096565B2

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