Phenylboronic Acid → HCID 69171162, Verbindung

HRID 2374449

Reaktionsgleichung

Reaktionsgleichung von HRID 2374449
[C:1]([O:5][C:6](=[O:32])[CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24](Cl)=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=3)[CH:15]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2].[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C1(P(C2C=CC=CC=2C2C=CC=CC=2)C2CCCCC2)CCCCC1.[F-].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2].C1COCC1>[C:1]([O:5][C:6](=[O:32])[CH2:7][CH2:8][N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[C:23]([C:28]([F:31])([F:30])[F:29])[CH:22]=3)[CH:15]=2)[CH2:10]1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 66827Phenylboronic AcidHCID 522689Potassium FluorideHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 691740893-[6-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid tert-butyl ester

Produkt 1

HCID 69171162HCID 69171162, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A microwave vial is charged with 3-[6-(4-chloro-3-trifluoromethyl-phenoxymethyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid tert-butyl ester (56 mg, 0.119 mmol), phenylboronic acid (17 mg, 1.2 eq.), Pd(OAc)2 (1.3 mg, 5 mol %), (dicyclohexylphosphino)biphenyl (4.2 mg, 10 mol %), KF (21 mg, 3 eq.), and THF (0.25 mL). The resulting mixture is heated to 120° C. using microwave irradiation for 20 minutes. The mixture is filtered through celite. The celite is washed with EtOAc several times. The filtrate is then concentrated to give a dark oil. The mixture is purified by column chromatography (silica gel, EtOAc/Hexane, gradient) to give 3-[6-(2-trifluoromethyl-biphenyl-4-yloxymethyl)-3,4-dihydro-1H-isoquinolin-2-yl]-propionic acid tert-butyl ester.

Aufarbeitung

  1. custommicrowave irradiation for 20 minutes
  2. filtrationThe mixture is filtered through celite
  3. washThe celite is washed with EtOAc several times
  4. concentrationThe filtrate is then concentrated
  5. customto give a dark oil
  6. customThe mixture is purified by column chromatography (silica gel, EtOAc/Hexane, gradient)

Quellen und Nachweise

ORD-Eintrag
ord-c6932c5e352b4a79b4e1aefcbc705ecf
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07462629B2

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