Cesium carbonate → 6-(3-Chloro-phenyl)-5-(3,3-difluoro-azetidin-1-yl)-pyridine-2-carboxylic acid

HRID 927564

Reaktionsgleichung

C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:14][C:13]([F:16])([F:15])[CH2:12]2)=[C:7](Cl)[N:6]=1)=[O:4].C(=O)([O-])[O-].[Cs+].[Cs+].[Cl:24][C:25]1[CH:26]=[C:27](B(O)O)[CH:28]=[CH:29][CH:30]=1>O.CN(C=O)C.C(Cl)Cl.[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[Cl:24][C:25]1[CH:30]=[C:29]([C:7]2[N:6]=[C:5]([C:3]([OH:2])=[O:4])[CH:10]=[CH:9][C:8]=2[N:11]2[CH2:14][C:13]([F:16])([F:15])[CH2:12]2)[CH:28]=[CH:27][CH:26]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

6-Chloro-5-(3,3-difluoroazetidin-1-yl)-pyridine-2-carboxylic acid methyl ester (Example 69 a, 0.3 g, 1.15 mmol), 1,1′-bis(diphenylphosphino)ferrocene-palladium(II)dichloride methylene chloride complex (CAN 72287-26-4, 47 mg, 0.058 mmol) and cesium carbonate (CAN 534-17-8, 0.56 g, 1.72 mmol) were added to a solution of 3-chlorophenylboronic acid (CAN 63503-60-6, 0.27 g, 1.72 mmol) in water (20 mL) and DMF (10 mL). The mixture was stirred for 48 h at 100° C. The reaction mixture was adjusted to pH=3 and extracted with methylene chloride (3×20 mL). The organic layers were combined, dried over sodium sulfate and concentrated to give the crude product (110 mg, 30%); MS (EI): 325.0 [M+H]+.

Aufarbeitung

extractionextracted with methylene chloride (3×20 mL)
dry with materialdried over sodium sulfate
concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag: ord-1e0606d1665f4c8bb95f52f40340ce40
Quelldatensatz: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09290451B2

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