4-Fluoro-2-methylaniline → HCID 57708076, Verbindung

HRID 659711

Reaktionsgleichung

Cl[C:2]1[C:3]2[CH:12]=[N:11][N:10]([C:13]3[C:18]([F:19])=[CH:17][CH:16]=[CH:15][C:14]=3[F:20])[C:4]=2[N:5]([CH3:9])[C:6](=[O:8])[CH:7]=1.CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[F:55][C:56]1[CH:62]=[CH:61][C:59]([NH2:60])=[C:58]([CH3:63])[CH:57]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[F:20][C:14]1[CH:15]=[CH:16][CH:17]=[C:18]([F:19])[C:13]=1[N:10]1[C:4]2[N:5]([CH3:9])[C:6](=[O:8])[CH:7]=[C:2]([NH:60][C:59]3[CH:61]=[CH:62][C:56]([F:55])=[CH:57][C:58]=3[CH3:63])[C:3]=2[CH:12]=[N:11]1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of 4-chloro-1-(2,6-difluorophenyl)-7-methyl-1H-pyrazolo[3,4-b]pyridin-6(7H)-one (36 mg, 0.1 mmol), tris(dibenzylideneacetone)dipalladium (0) (6 mg, 0.006 mmol), X-Phos (6 mg) and 4-fluoro-2-methylaniline (3 mg, 0.2 mmol) in toluene (3 mL) was treated with sodium t-butoxide (40 mg, 0.4 mmol), and heated to 100° C. for 18 h. After the mixture was cooled to RT, it was evaporated to dryness with some silica gel, and purified by silica gel chromatography to provide the title compound as an off-white crystalline solid. MS (ESI, pos.ion) m/z: 385.1 (M+1).

Aufarbeitung

temperatureAfter the mixture was cooled to RT
customit was evaporated to dryness with some silica gel
custompurified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag: ord-5bc5bf218a6642cf97fded15955dc0d4
Quelldatensatz: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08080546B2

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