2,3-Difluorophenylacetic acid → HCID 178520266, Verbindung

HRID 269519Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269519
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([OH:12])=O.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[NH:23]1[C:27]2=[N:28][CH:29]=[CH:30][CH:31]=[C:26]2[C:25](C(OCC)=O)=[N:24]1.N1C2=NC=CC=C2C(C(OC(C)C)=O)=N1>C1COCC1>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][C:10]([C:25]1[C:26]2[C:27](=[N:28][CH:29]=[CH:30][CH:31]=2)[NH:23][N:24]=1)=[O:12]

Komponenten

6

Edukt 4

HCID 5207722,3-Difluorophenylacetic acidHCID 2733832Lithium HexamethyldisilazideHCID 178459485HCID 178459485, VerbindungHCID 178470482Ethyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate

Produkt 1

HCID 178520266HCID 178520266, VerbindungAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Versuchsvorschrift

To a solution of 2,3-difluorophenylacetic acid (236 mg, 1.4 mmol) in THF at OC was added 3.85 mL (3.85 mmol) of a solution of lithium bis-trimethylsilylamide in THF. The resulting solution was then added to solution of a 2:1 mixture of ethyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate and isopropyl 1H-pyrazolo[3,4-b]pyridine-3-carboxylate (104 mg, 0.55 mmol) in THF. The resulting mixture was heated at 75C for 3 hours. The reaction progress was monitored by TLC and HPLC and quenched with saturated NH4Cl, diluted with EtOAc and washed with saturated NaHCO3 and brine. The organic layer was dried over MgSO4 and concentrated to give 137 mg (91% yield) of 2-(2,3-difluorophenyl)-1-(1H-pyrazolo[3,4-b]pyridin-3-yl)ethanone. LC-MS Rt=3.3 min ES+ (274.0) ES− (272.1).

Aufarbeitung

  1. customquenched with saturated NH4Cl
  2. additiondiluted with EtOAc
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialThe organic layer was dried over MgSO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-7c485fca78ec40f4b6af520267262c41
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446199B2

Notizen zur Reaktion

Wird geladen…