Cesium carbonate → 5'-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-one

HRID 472998Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 472998
Br[C:2]1[CH:3]=[CH:4][C:5]2[O:9][C:8]3([CH2:15][CH2:14][C:13]4[CH:16]=[CH:17][CH:18]=[CH:19][C:12]=4[CH2:11][CH2:10]3)[C:7](=[O:20])[C:6]=2[CH:21]=1.[Cl:22][C:23]1[CH:24]=[C:25](B(O)O)[CH:26]=[C:27]([F:29])[CH:28]=1.C([O-])([O-])=O.[Cs+].[Cs+].O1CCOCC1>C(Cl)Cl.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:22][C:23]1[CH:24]=[C:25]([C:2]2[CH:3]=[CH:4][C:5]3[O:9][C:8]4([CH2:10][CH2:11][C:12]5[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=5[CH2:14][CH2:15]4)[C:7](=[O:20])[C:6]=3[CH:21]=2)[CH:26]=[C:27]([F:29])[CH:28]=1

Komponenten

8

Edukt 4

HCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 15391287(3-Chloro-5-fluorophenyl)boronic acidHCID 581970305'-bromo-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-one

Produkt 1

HCID 581980625'-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-oneAusbeute 92,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418476HCID 178418476, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A 10 mL microwave tube was charged with 5′-bromo-5,6,8,9-tetrahydro-3′H-spiro[benzo[7]annulene-7,2′-benzofuran]-3′-one (0.0573 g, 0.167 mmol), 3-chloro-5-fluorophenylboronic acid (0.0930 g, 0.53 mmol), Cs2CO3 (0.2537 g, 0.78 mmol), 1,4-dioxane (4 mL), water (1 mL), and PdCl2(PPh3)2 (0.0118 g, 0.0168 mmol). The tube was heated in a CEM microwave reactor at 110° C. for 30 min. The reaction mixture was diluted with CH2Cl2 and dried over Na2SO4. After the solvent was evaporated under reduced pressure, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford 0.0607 g (92%) of 5′-(3-chloro-5-fluorophenyl)-5,6,8,9-tetrahydro-3′H-spiro[benzo[7]annulene-7,2′-benzofuran]-3′-one. LC-MS tR=2.55 min in 3 min chromatography, m/z 393, 395 (MH+).

Aufarbeitung

  1. dry with materialdried over Na2SO4
  2. customAfter the solvent was evaporated under reduced pressure
  3. customthe residue was purified by chromatography on silica gel
  4. washeluted with hexanes/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c5f8b9d8c4a44e2e9effa3dc696bcc63
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08633212B2

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