Water → 4-(1,3-Dimethyl-1H-pyrazol-4-ylmethyl)-3'-(4-chloro-3-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

HRID 220533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220533
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][C:3]=1[F:11].Cl[C:13]1[C:14]([N:19]2[CH2:24][CH2:23][N:22]([CH2:25][C:26]3[C:27]([CH3:32])=[N:28][N:29]([CH3:31])[CH:30]=3)[CH2:21][CH2:20]2)=[N:15][CH:16]=[CH:17][N:18]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C(=O)C.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>[CH3:31][N:29]1[CH:30]=[C:26]([CH2:25][N:22]2[CH2:21][CH2:20][N:19]([C:14]3[C:13]([C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([F:11])[CH:4]=4)=[N:18][CH:17]=[CH:16][N:15]=3)[CH2:24][CH2:23]2)[C:27]([CH3:32])=[N:28]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27786564-Chloro-3-fluorophenylboronic AcidHCID 866416563'-Chloro-4-(1,3-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazine

Produkt 1

HCID 593217634-(1,3-Dimethyl-1H-pyrazol-4-ylmethyl)-3'-(4-chloro-3-fluorophenyl)-3,4,5,6-tetrahydro-2H-[1,2']bipyrazineAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 31374DimethylacetamideLösungsmittel

Versuchsvorschrift

Add 4-chloro-3-fluorobenzeneboronic acid (125 mg, 0.72 mmol) to a nitrogen purged solution of 3′-chloro-4-(1,3-dimethyl-1H-pyrazol-4-ylmethyl)-3,4,5,6-tetrahydro-2H-[1,2′]bipyrazinyl (200 mg, 0.65 mmol) in dry N,N-dimethylacetamide (4 mL) and deoxygenated water (2 mL). Add potassium carbonate (215 mg, 1.72 mmol) then tetrakis(triphenylphosphine)palladium(0) (0.004 g, 0.0035 mmol) and stir at 110° C. for 6 hr. Cool to room temperature, add water (10 mL) and extract with DCM (3×20 mL). Concentrate the combined DCM extracts and purify by reverse phase HPLC to give the title compound (0.036 g, 14%). MS (ES): m/z=401 [M+H]+

Aufarbeitung

  1. customdeoxygenated water (2 mL)
  2. extractionextract with DCM (3×20 mL)
  3. concentrationConcentrate the combined DCM extracts
  4. custompurify by reverse phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-36626122de3d4f8682d0e2eb4b099977
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202873B2

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