Water → N-acetyl-N-(4-bromoisoquinolin-1-yl)acetamide

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Reaktionsgleichung

[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH2:12])=[N:4][CH:3]=1.C(N([CH2:20][CH3:21])C(C)C)(C)C.[C:22](Cl)(=[O:24])[CH3:23].[OH2:26]>C(Cl)Cl>[C:22]([N:12]([C:5]1[C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]([Br:1])=[CH:3][N:4]=1)[C:20](=[O:26])[CH3:21])(=[O:24])[CH3:23]

Komponenten

Reaktionsbedingungen

Temperatur: 0 °C

Versuchsvorschrift

To a solution of 4-bromoisoquinolin-1-amine (403 mg, 1.81 mmol) in methylene chloride (11 mL) at 0° C. was added N,N-diisopropylethylamine (1.57 mL, 9.03 mmol), followed by acetyl chloride (0.321 mL, 4.52 mmol) dropwise. The mixture was stirred at 0° C. for 10 min then at room temperature for 2 h. The mixture was diluted with DCM (10 mL). Water (20 mL) was added. The organic layer was separated. The aqueous solution was extracted with DCM (10 mL). The combined DCM solutions were dried (Na2SO4). After filtration and concentration, the crude was purified with flash chromatography to give the desired product (470 mg, 85%). 1H NMR (400 MHz, DMSO) δ 8.79 (s, 1H), 8.23 (d, J=8.4, 1H), 8.13 (d, J=8.4, 1H), 8.05 (t, J=7.7, 1H), 7.87 (t, J=7.6, 1H), 2.23 (s, 6H).

Aufarbeitung

waitat room temperature for 2 h
customThe organic layer was separated
extractionThe aqueous solution was extracted with DCM (10 mL)
dry with materialThe combined DCM solutions were dried (Na2SO4)
filtrationAfter filtration and concentration
customthe crude was purified with flash chromatography

Quellen und Nachweise

ORD-Eintrag: ord-5b0d66967ad04c65bd82509cfc9a1a0e
Quelldatensatz: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08173650B2

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