Potassium Phosphate, Tribasic → 6-(2,6-difluoro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 1778684Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1778684
Cl[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:4]=2[CH:3]=1.[F:17][C:18]1[C:23]([O:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[C:20]([F:28])[C:19]=1B1OC(C)(C)C(C)(C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>O1CCCC1.O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.NC1C=CC=CC=1C1C=CC=CC=1[Pd]Cl>[F:17][C:18]1[C:23]([O:24][CH3:25])=[CH:22][C:21]([O:26][CH3:27])=[C:20]([F:28])[C:19]=1[C:2]1[N:7]=[CH:6][C:5]2[CH:8]=[N:9][N:10]([CH:11]3[CH2:16][CH2:15][CH2:14][CH2:13][O:12]3)[C:4]=2[CH:3]=1

Komponenten

7

Edukt 3

HCID 62657Potassium Phosphate, TribasicHCID 714636356-Chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridineHCID 867228062-(2,6-Difluoro-3,5-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

Produkt 1

HCID 867228166-(2,6-difluoro-3,5-dimethoxyphenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridineAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178439015HCID 178439015, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A mixture of 6-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[4,3-c]pyridine (333 mg, 1.40 mmol), 2-(2,6-difluoro-3,5-dimethoxyphenyl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (400.0 mg, 1.333 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine-(2′-aminobiphenyl-2-yl)(chloro)palladium (1:1) (21.0 mg, 0.0266 mmol), and potassium phosphate (566 mg, 2.66 mmol) in tetrahydrofuran (3 mL) and water (5.5 mL) in a reaction vial was degassed and sealed. The mixture was stirred at r.t. for 30 min. The mixture was extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (gradient: 0-50%) to afford the desired product (0.38 g, 76%). LCMS (M+H)+=376.1.

Aufarbeitung

  1. customvial was degassed
  2. customsealed
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (gradient: 0-50%)

Quellen und Nachweise

ORD-Eintrag
ord-b272352bc29c4f2397a149a3a4261408
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266892B2

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