Cesium carbonate → 3-(1-Hydroxyethyl)-4-(4-(2-morpholinoethoxy)phenyl)-1H-isochromen-1-one

HRID 634362

Reaktionsgleichung

Reaktionsgleichung von HRID 634362
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[O:4][C:3]=1[CH:13]([OH:15])[CH3:14].CC1(C)C(C)(C)OB([C:24]2[CH:38]=[CH:37][C:27]([O:28][CH2:29][CH2:30][N:31]3[CH2:36][CH2:35][O:34][CH2:33][CH2:32]3)=[CH:26][CH:25]=2)O1.C([O-])([O-])=O.[Cs+].[Cs+]>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>[OH:15][CH:13]([C:3]1[O:4][C:5](=[O:12])[C:6]2[C:11]([C:2]=1[C:24]1[CH:38]=[CH:37][C:27]([O:28][CH2:29][CH2:30][N:31]3[CH2:32][CH2:33][O:34][CH2:35][CH2:36]3)=[CH:26][CH:25]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH3:14]

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 46259104-(2-Morpholin-4-ylethoxy)benzeneboronic acid, pinacol esterHCID 1181312554-Bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one2×

Produkt 1

HCID 1181313013-(1-Hydroxyethyl)-4-(4-(2-morpholinoethoxy)phenyl)-1H-isochromen-1-oneAusbeute 33,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 178418397HCID 178418397, VerbindungKatalysator

Versuchsvorschrift

The title compound was made in a similar way as that of the intermediate B1, using 4-bromo-3-(1-hydroxyethyl)-1H-isochromen-1-one (Intermediate A2, 0.36 g, 1.35 mmol), 4-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethyl)-morpholine (0.45 g, 1.35 mmol), Pd(PPh3)4 (0.078 g, 0.068 mmol) and Cs2CO3 (0.53 g, 1.6 mmol). The crude was filtered, diluted with 1M HClaqueous (3 ml) and purified via reverse phase chromatography with a Biotage C18 SNAP 120 g column (Phase A, water 95%, ACN 4.9%, formic acid 0.1%); Phase B ACN 99.9%, formic acid 0.1%) to afford the title compound (0.179 g, 33%).

Aufarbeitung

  1. filtrationThe crude was filtered
  2. additiondiluted with 1M HClaqueous (3 ml)
  3. custompurified via reverse phase chromatography with a Biotage C18 SNAP 120 g column (Phase A, water 95%, ACN 4.9%, formic acid 0.1%)

Quellen und Nachweise

ORD-Eintrag
ord-afa818dd489e4ba094a373f5f0c4aa08
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321776B2

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