Sodium Carbonate → 2,2-Dimethyl-n-(6-thiomorpholin-4-yl-4-o-tolyl-pyridin-3-yl)-propionamide

HRID 22644

Reaktionsgleichung

I[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][S:11][CH2:10][CH2:9]2)[N:5]=[CH:4][C:3]=1[NH:14][C:15](=[O:20])[C:16]([CH3:19])([CH3:18])[CH3:17].C(=O)([O-])[O-].[Na+].[Na+].[C:27]1([CH3:36])[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=1B(O)O>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.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH3:17][C:16]([CH3:19])([CH3:18])[C:15]([NH:14][C:3]1[CH:4]=[N:5][C:6]([N:8]2[CH2:13][CH2:12][S:11][CH2:10][CH2:9]2)=[CH:7][C:2]=1[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][C:27]=1[CH3:36])=[O:20]

Komponenten

Reaktionsbedingungen

Temperatur: 80 °C

Versuchsvorschrift

A mixture of 4.05 g (10.0 mmol) N-(4-iodo-6-thiomorpholin-4-yl-pyridin-3-yl)-2,2-dimethyl-propionamide, 54 ml toluene, 16 ml 2 N sodium carbonate solution, 347 mg (0.3 mmol) tetrakis(triphenylphosphine)palladium(0), 67 mg (0.3 mmol) palladium(II) acetate and 1.50 g (11.0 mmol) o-tolylboronic acid was heated under argon at 80° C. for 18 h. After cooling to room temperature, the aqueous phase was separated and washed twice with ethyl acetate. The combined organic layers were washed with 50 ml brine, dried (sodium sulfate) and evaporated. Purification by flash-chromatography gave 3.57 g (quantitative) of the title compound as a light brown solid.

Aufarbeitung

temperatureAfter cooling to room temperature
customthe aqueous phase was separated
washwashed twice with ethyl acetate
washThe combined organic layers were washed with 50 ml brine
dry with materialdried (sodium sulfate)
customevaporated
customPurification by flash-chromatography

Quellen und Nachweise

ORD-Eintrag: ord-cc3b350c60d249e1a0c9ddbd7e0f52b9
Quelldatensatz: uspto-grants-2005_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06849624B2

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