Dimethyl Sulfoxide → [6-[2-[Methyl-[(2-methylpropan-2-yl)oxycarbonyl]amino]propanoylamino]-2-(2-phenylethynyl)pyridin-3-yl]boronic acid

HRID 535395

Reaktionsgleichung

[C:1]([O:5][C:6](=[O:29])[N:7]([CH:9]([CH3:28])[C:10]([NH:12][C:13]1[CH:18]=[CH:17][C:16](Br)=[C:15]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:14]=1)=[O:11])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[B:30]1(B2OCC(C)(C)CO2)[O:35]CC(C)(C)C[O:31]1.CC([O-])=O.[K+].CS(C)=O>O.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[Pd]Cl>[CH3:8][N:7]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:29])[CH:9]([CH3:28])[C:10]([NH:12][C:13]1[N:14]=[C:15]([C:20]#[C:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]([B:30]([OH:35])[OH:31])=[CH:17][CH:18]=1)=[O:11]

Komponenten

Reaktionsbedingungen

Temperatur: 65 °C

Versuchsvorschrift

A mixture of tert-butyl-N-[1-[[5-bromo-6-(2-phenylethynyl)pyridin-2-yl]amino]-1-oxopropan-2-yl]-N-methylcarbamate C2a (2.5 g, 5.45 mmol), bis(neopentyl glycolato)diboron (2.46 g, 10.9 mmol), KOAc (1.61 g, 16.4 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (399 mg, 0.55 mmol) and DMSO (20 ml) is stirred under argon atmosphere for 39 h at 65° C. The mixture is diluted with water and extracted with DCM. The combined organic layers are dried over MgSO4, concentrated in vacuo and the product purified by RP HPLC. Yield: 1.73 g (75%). HPLC-MS: M+H=424; tR=1.59 min (*Method—5).

Aufarbeitung

extractionextracted with DCM
dry with materialThe combined organic layers are dried over MgSO4
concentrationconcentrated in vacuo
customthe product purified by RP HPLC

Quellen und Nachweise

ORD-Eintrag: ord-9051c5d5e0f34b2683364f12abbee8e0
Quelldatensatz: uspto-grants-2014_10
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08859541B2

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