Cesium carbonate → HCID 69069566, Verbindung

HRID 216198

Reaktionsgleichung

Reaktionsgleichung von HRID 216198
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][C:14]=2[F:23])[CH:3]=1.[OH:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1.C([O-])([O-])=O.[Cs+].[Cs+]>COCCOC.O.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>[F:23][C:14]1[CH:15]=[C:16]([C:19]([F:22])([F:21])[F:20])[CH:17]=[CH:18][C:13]=1[CH2:12][CH2:11][NH:10][C:4]1[N:5]=[C:6]([O:8][CH3:9])[N:7]=[C:2]([C:29]2[CH:30]=[C:25]([OH:24])[CH:26]=[CH:27][CH:28]=2)[CH:3]=1

Komponenten

7

Edukt 3

HCID 10796Cesium carbonateHCID 2734359(3-hydroxyphenyl)boronic AcidHCID 57636111HCID 57636111, Verbindung

Produkt 1

HCID 69069566HCID 69069566, VerbindungAusbeute 116,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

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

Versuchsvorschrift

A mixture of (6-chloro-2-methoxy-pyrimidin-4-yl)-[2-(2-fluoro-4-trifluoromethyl-phenyl)-ethyl]-amine [1.47 g, 4.2 mmol, see Example 52, step 1], (3-hydroxy-phenyl)-boronic acid, (637 mg, 4.62 mmol), and Cs2CO3 (3.4 g, 10.5 mmol) in ethylene glycol dimethyl ether (20 mL) and water (4 mL) is degassed by bubbling with Argon gas for 5 minutes, and treated with tetrakis(triphenylphosphine)palladium(0) (243 mg, 0.21 mmol) at room temperature. After 15 h at 85° C., the mixture is diluted with water (50 mL), and extracted with EtOAc (2×50 mL). The extracts are dried (MgSO4), filtered through a pad of SiO2, and concentrated to afford 3-{6-[2-(2-fluoro-4-trifluoromethyl-phenyl)-ethylamino]-2-methoxy-pyrimidin-4-yl}-phenol (2 g). LCMS: RT=2.32 minutes; MS: 408 (M+H).

Aufarbeitung

  1. customis degassed
  2. customby bubbling with Argon gas for 5 minutes
  3. extractionextracted with EtOAc (2×50 mL)
  4. dry with materialThe extracts are dried (MgSO4)
  5. filtrationfiltered through a pad of SiO2
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-90a700f5e5434463bcfcde32570cadbc
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193183B2

Verknüpfte Notizen

Wird geladen…