Binap, (A+-)- → N-[4-Chloro-2-(6-methyl-pyridine-3-carbonyl)-phenyl]-4-(cis-2,6-dimethyl-morpholin-4-yl)-3-fluoro-benzenesulfonamide

HRID 29544

Reaktionsgleichung

Reaktionsgleichung von HRID 29544
Br[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:13]=2[C:19]([C:21]2[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=2)=[O:20])(=[O:10])=[O:9])=[CH:4][C:3]=1[F:28].O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:84][C@H:85]1[O:90][C@@H:89]([CH3:91])[CH2:88][NH:87][CH2:86]1>CN(C=O)C.[Pd]>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([NH:11][S:8]([C:5]2[CH:6]=[CH:7][C:2]([N:87]3[CH2:86][C@H:85]([CH3:84])[O:90][C@H:89]([CH3:91])[CH2:88]3)=[C:3]([F:28])[CH:4]=2)(=[O:10])=[O:9])=[C:13]([C:19]([C:21]2[CH:22]=[N:23][C:24]([CH3:27])=[CH:25][CH:26]=2)=[O:20])[CH:14]=1

Komponenten

7

Edukt 4

HCID 634876Binap, (A+-)-HCID 6415002,6-Dimethylmorpholine, cis-HCID 22031701Potassium phosphate, tribasic, monohydrateHCID 597885734-Bromo-N-[4-chloro-2-(6-methyl-pyridine-3-carbonyl)-phenyl]-3-fluoro-benzenesulfonamide

Produkt 1

HCID 59788542N-[4-Chloro-2-(6-methyl-pyridine-3-carbonyl)-phenyl]-4-(cis-2,6-dimethyl-morpholin-4-yl)-3-fluoro-benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The title compound was prepared according to the general procedure for the synthesis of heterocyclyl and heteroaryl substituted phenylsulfonyl derivatives previously described, using 4-Bromo-N-[4-chloro-2-(6-methyl-pyridine-3-carbonyl)-phenyl]-3-fluoro-benzenesulfonamide 0.2 g (0.4 mmol), potassium phosphate tribasic monohydrate 0.570 g (2.4 mmol), rac-2,2′-bis (diphenylphosphino)-1,1′-binaphthyl 0.077 g (0.12 mmol), cis-2,6-dimethyl-morpholine 0.23 g (2 mmol) and Pd (dba)3 0.057 g (0.06 mmol) in 2 ml DMF. HPLC purification gave yellow compound.

Aufarbeitung

  1. customHPLC purification
  2. customgave yellow compound

Quellen und Nachweise

ORD-Eintrag
ord-5bba3fa6d3cb45bfbb0167fa9013705c
Quelldatensatz
uspto-grants-2008_09
Patentnummer
US07420055B2

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