Cesium carbonate → (2-{2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl}phenyl)-methanol

HRID 8589

Reaktionsgleichung

Reaktionsgleichung von HRID 8589
Br[C:2]1[CH:3]=[N:4][C:5]([C:8]2[C:16]3[C:11](=[N:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[F:24])[N:9]=2)=[N:6][CH:7]=1.[OH:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O.C(=O)([O-])[O-].[Cs+].[Cs+]>COCCOC>[F:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH2:17][N:10]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:16]2[C:8]([C:5]2[N:4]=[CH:3][C:2]([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=3[CH2:26][OH:25])=[CH:7][N:6]=2)=[N:9]1

Komponenten

5

Edukt 3

HCID 10796Cesium carbonateHCID 43742622-(Hydroxymethyl)phenylboronic AcidHCID 115890733-(5-Bromo-2-pyrimidinyl)-1-(2-fluorobenzyl)-1H-pyrazolo[3,4-b]pyridine

Produkt 1

HCID 21983543(2-{2-[1-(2-Fluorobenzyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-5-pyrimidinyl}phenyl)-methanol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

200 mg (0.52 mmol) of 3-(5-bromo-2-pyrimidinyl)-1-(2-fluorobenzyl)-1H-pyrazolo-[3,4-b]pyridine (example I, step 6), 90 mg (0.62 mmol) of 2-(hydroxymethyl)-phenylboronic acid, 40 mg (0.05 mmol) of 1,1′-bis(diphenylphosphino)-ferrocenepalladium(II) chloride and 200 mg (0.62 mmol) of cesium carbonate are taken up in 2 ml of DME and stirred under reflux overnight. The solvent is removed under vacuum, and the residue is purified by preparative HPLC to result in 111 mg (52% of theory) of the product.

Aufarbeitung

  1. temperatureunder reflux overnight
  2. customThe solvent is removed under vacuum
  3. customthe residue is purified by preparative HPLC
  4. customto result in 111 mg (52% of theory) of the product

Quellen und Nachweise

ORD-Eintrag
ord-1b2965c8ee8a4c30837640f4245842fe
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091198B1

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