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Sodium Carbonate → (S)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-1-(1-(5-phenylpyrimidin-2-yl)piperidin-4-yl)pyrrolidin-2-one

HRID 407978
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 407978
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([N:14]3[CH2:18][CH2:17][C@H:16]([O:19][C:20]4[CH:25]=[C:24]([F:26])[C:23]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:22][C:21]=4[F:31])[C:15]3=[O:32])[CH2:10][CH2:9]2)=[N:6][CH:7]=1.[C:33]1(B(O)O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.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:31][C:21]1[CH:22]=[C:23]([S:27]([CH3:30])(=[O:29])=[O:28])[C:24]([F:26])=[CH:25][C:20]=1[O:19][C@H:16]1[CH2:17][CH2:18][N:14]([CH:11]2[CH2:12][CH2:13][N:8]([C:5]3[N:4]=[CH:3][C:2]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:7][N:6]=3)[CH2:9][CH2:10]2)[C:15]1=[O:32]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 67469711(S)-1-(1-(5-bromopyrimidin-2-yl)piperidin-4-yl)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)pyrrolidin-2-one

Produkt 1

HCID 54671279(S)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-1-(1-(5-phenylpyrimidin-2-yl)piperidin-4-yl)pyrrolidin-2-oneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397
HCID 178418397, Verbindung
Katalysator
HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

(S)-1-(1-(5-bromopyrimidin-2-yl)piperidin-4-yl)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)pyrrolidin-2-one (Example 90; 80 mg, 0.15 mmol) was dissolved in dioxane (2 mL) and phenylboronic acid (28 mg, 0.23 mmol), 2M Na2CO3 (301 μL, 0.60 mmol) and Pd(PPh3)4 (17 mg, 0.015 mmol) were added and the reaction heated to 95° C. under nitrogen for 2 hours. The reaction was cooled to ambient temperature and partitioned between water and CH2Cl2, and the organic layers were dried over Na2SO4, filtered and concentrated. The residue was purified over silica gel (70% EtOAc in hexanes) to afford impure material. The material was then purified on C18 reverse phase chromatography (20 to 95% ACN in water) to afford (S)-3-(2,5-difluoro-4-(methylsulfonyl)phenoxy)-1-(1-(5-phenylpyrimidin-2-yl)piperidin-4-yl)pyrrolidin-2-one (51 mg, 0.096 mmol, 64% yield) as a white solid. Mass spectrum (apci) m/z=529.3 (M+H).

Aufarbeitung

  1. temperatureThe reaction was cooled to ambient temperature
  2. custompartitioned between water and CH2Cl2
  3. dry with materialthe organic layers were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified over silica gel (70% EtOAc in hexanes)
  7. customto afford impure material
  8. customThe material was then purified on C18 reverse phase chromatography (20 to 95% ACN in water)

Quellen und Nachweise

ORD-Eintrag
ord-d366e03f18c34d7a864386e652c2a060
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08754226B2

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