Sodium Carbonate → 4-(4'-Chlorobiphenyl-4-yloxy)-1-pyridin-3-yl-pentan-3-ol

HRID 379981

Reaktionsgleichung

Reaktionsgleichung von HRID 379981
[Si]([O:8][C@H:9]([CH2:22][CH2:23][C:24]1[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=1)[C@H:10]([CH3:21])[O:11][C:12]1[CH:17]=[CH:16][C:15](B(O)O)=[CH:14][CH:13]=1)(C(C)(C)C)(C)C.[Cl:30][C:31]1[CH:36]=[CH:35][C:34](I)=[CH:33][CH:32]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.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>[Cl:30][C:31]1[CH:36]=[CH:35][C:34]([C:15]2[CH:14]=[CH:13][C:12]([O:11][CH:10]([CH3:21])[CH:9]([OH:8])[CH2:22][CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[CH:17][CH:16]=2)=[CH:33][CH:32]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 125101-Chloro-4-iodobenzeneHCID 54020751(1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid

Produkt 1

HCID 183675944-(4'-Chlorobiphenyl-4-yloxy)-1-pyridin-3-yl-pentan-3-ol

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

Prepared according to the method described in Example 12b) from (1S,2R)-4-[2-(tert-butyldimethylsilanyloxy)-1-methyl-4-pyridin-3-ylbutoxy]benzeneboronic acid (0.20 g, Example 11)), 4-chloro-iodobenzene (0.24 g), 2M aqueous sodium carbonate (0.5 ml) and tetrakis(triphenylphosphine)palladium (0) (0.1 g) in toluene (4 ml) and ethanol (1 ml). The reaction mixture was heated at 100° C. for 4 hours. After cooling, the solution was concentrated under reduced pressure. Concentrated hydrochloric acid (1 ml) was added to a solution of the residue in methanol (5 ml) and the suspension was stirred at room temperature for 3 hours. After work up, the residue was purified by normal-phase HPLC eluting with a gradient of 0-25% ethanol in dichloromethane to give a gum, from which the oxalate salt was made (0.11 g).

Aufarbeitung

  1. customPrepared
  2. temperatureAfter cooling
  3. concentrationthe solution was concentrated under reduced pressure
  4. additionConcentrated hydrochloric acid (1 ml) was added to a solution of the residue in methanol (5 ml)
  5. customAfter work up, the residue was purified by normal-phase HPLC
  6. washeluting with a gradient of 0-25% ethanol in dichloromethane
  7. customto give a gum

Quellen und Nachweise

ORD-Eintrag
ord-92b59a4f959849e1a50f7c4069bcf7a7
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300352B1

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