Potassium Phosphate, Tribasic → HCID 178466665, Verbindung

HRID 2114568Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2114568
[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[NH:11][N:12]=[CH:13][C:8]2=[C:7]([NH:14][CH2:15][CH:16]([OH:19])[CH2:17]I)[N:6]=1.[F:25][C:26]1[CH:27]=[CH:28][C:29]([O:35][CH2:36][CH3:37])=[C:30](B(O)O)[CH:31]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1>[F:1][C:2]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:3]=1[O:4][C:5]1[N:10]=[C:9]2[NH:11][N:12]=[C:13]([C:28]3[CH:27]=[C:26]([F:25])[CH:31]=[CH:30][C:29]=3[O:35][CH2:36][CH3:37])[C:8]2=[C:7]([NH:14][CH2:15][C@H:16]([OH:19])[CH3:17])[N:6]=1

Komponenten

5

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 16217479(2-Ethoxy-5-fluorophenyl)boronic acidHCID 866004866-(2,4-Difluoro-phenoxy)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino-propan-2-ol

Produkt 1

HCID 178466665HCID 178466665, VerbindungAusbeute 30,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
180 °C

Versuchsvorschrift

1-[6-(2,4-Difluoro-phenoxy)-3-iodo-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino-propan-2-ol (200 mg, 0.447 mmol), 5-fluoro-2-ethoxyphenyl boronic acid (246 mg), K3PO4 (285 mg), and Tetrakis(triphenylphosphine) palladium(0) CH2Cl2 (73 mg) were added to 2 mL dioxane in a microwave vial. The vial was sealed and the reaction mixture was heated to 180° C. for 10 minutes. The reaction mixture was partitioned between water and ethyl acetate, and the organic layer was separated, dried over MgSO4, filtered, and evaporated under reduced pressure. The residue was filtered through silica gel using 10% MeOH in methylene chloride, then purified by preparative scale thin layer chromatography using 10% MeOH in methylene chloride, to give 62.9 mg of (R)-1-[6-(2,4-Difluoro-phenoxy)-3-(2-ethoxy-5-fluoro-phenyl)-1H-pyrazolo[3,4-d]pyrimidin-4-ylamino]-propan-2-ol. Mass Spec. M+H=460.

Aufarbeitung

  1. customThe vial was sealed
  2. customThe reaction mixture was partitioned between water and ethyl acetate
  3. customthe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. filtrationThe residue was filtered through silica gel using 10% MeOH in methylene chloride
  8. custompurified by preparative scale thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-3ca40e5d5348429f8408ee7b71877e88
Quelldatensatz
uspto-grants-2008_10
Patentnummer
US07435731B2

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