Cesium carbonate → 2-(5-fluoropyridin-3-ylamino)-N-methyl-3-nitrobenzamide

HRID 2036636

Reaktionsgleichung

C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.Br[C:50]1[C:59]([N+:60]([O-:62])=[O:61])=[CH:58][CH:57]=[CH:56][C:51]=1[C:52]([NH:54][CH3:55])=[O:53].[F:63][C:64]1[CH:65]=[C:66]([NH2:70])[CH:67]=[N:68][CH:69]=1>C1(C)C=CC=CC=1.CCOC(C)=O.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:63][C:64]1[CH:65]=[C:66]([NH:70][C:50]2[C:59]([N+:60]([O-:62])=[O:61])=[CH:58][CH:57]=[CH:56][C:51]=2[C:52]([NH:54][CH3:55])=[O:53])[CH:67]=[N:68][CH:69]=1

Komponenten

Reaktionsbedingungen

Temperatur: 100 °C

Versuchsvorschrift

A mixture of cesium carbonate (1.55 g, 4.75 mmol), xantphos (550 mg, 0.950 mmol), 2-bromo-N-methyl-3-nitrobenzamide (820 mg, 3.17 mmol) (Prepared in Example 20), tris(dibenzylideneacetone)dipalladium (0) (580 mg, 0.63 mmol), 5-fluoropyridin-3-amine (532 mg, 4.75 mmol) in toluene (15 mL) under N2 was heated at 100° C. for 18 h. The mixture was cooled to rt and diluted with EtOAc. The mixture was filtered and the filtrates were concentrated in vacuo. Purification of the residue by flash chromatography over silica gel, using EtOAc as eluent gave 2-(5-fluoropyridin-3-ylamino)-N-methyl-3-nitrobenzamide: 1H NMR (400 MHz, CDCl3) δ 9.29 (1H, s), 8.23 (1H, s), 8.21 (1H, d, J=8.0 Hz), 8.16 (1H, s), 7.89 (1H, d, J=8.0 Hz), 7.26 (1H, t, J=8.0 Hz), 7.04 (1H, d, J=8.0 Hz), 6.41 (1H, br), 2.78 (3H, d, J=4.0 Hz); LC-MS (ESI) m/z 291.1 [M+H]+.

Aufarbeitung

temperatureThe mixture was cooled to rt
filtrationThe mixture was filtered
concentrationthe filtrates were concentrated in vacuo
customPurification of the residue by flash chromatography over silica gel

Quellen und Nachweise

ORD-Eintrag: ord-912c0b745a454fa8af239329721693bd
Quelldatensatz: uspto-grants-2013_11
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US08575183B2

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