Nitrogen → Methyl 6-(4-((dimethylamino)methyl)piperidin-1-yl)-1-isopropyl-1H-indazole-4-carboxylate

HRID 85450

Reaktionsgleichung

Br[C:2]1[CH:3]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]2[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=2[CH:10]=1.[CH3:18][N:19]([CH3:27])[CH2:20][CH:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1.C(=O)([O-])[O-].[Cs+].[Cs+].N#N.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>CO.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd].C1(C)C=CC=CC=1>[CH3:18][N:19]([CH2:20][CH:21]1[CH2:26][CH2:25][N:24]([C:2]2[CH:3]=[C:4]([C:14]([O:16][CH3:17])=[O:15])[C:5]3[CH:6]=[N:7][N:8]([CH:11]([CH3:13])[CH3:12])[C:9]=3[CH:10]=2)[CH2:23][CH2:22]1)[CH3:27]

Komponenten

Reaktionsbedingungen

Temperatur: 115 °C

Versuchsvorschrift

To a 10-mL microwave tube were added methyl 6-bromo-1-(1-methylethyl)-1H-indazole-4-carboxylate (250 mg, 0.841 mmol), N,N-dimethyl-1-(4-piperidinyl)methanamine (132 mg, 0.925 mmol), Toluene (3 mL), and cesium carbonate (411 mg, 1.262 mmol), and the mixture was degassed for 5 min by bubbling N2 through BINAP (79 mg, 0.126 mmol) and Pd2(dba)3 (38.5 mg, 0.042 mmol) were added. The tube was sealed and the mixture was heated at 115° C. with stirring for 15 h. The mixture was diluted with methanol (5 mL) and filtered. The filtrate was concentrated and the residue was purified using reverse-phase HPLC to give 35 mg of product as a off-white solid. LCMS MH+=359.3

Aufarbeitung

customthe mixture was degassed for 5 min
additionwere added
customThe tube was sealed
filtrationfiltered
concentrationThe filtrate was concentrated
customthe residue was purified

Quellen und Nachweise

ORD-Eintrag: ord-8419e21f691849a0a468bc7caa513bac
Quelldatensatz: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08846935B2

Verknüpfte Notizen

Wird geladen…