Binap, (A+-)- → (5-Chloro-4-dimethoxymethyl-pyridin-2-yl)-[(R)-1-(4-chloro-3-methyl-phenyl)-propyl]-amine

HRID 1629745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1629745
[CH2:1]([O:3][C:4]([C:6]1[C:11](C)=[CH:10][N:9]=[C:8](Cl)[CH:7]=1)=[O:5])C.[ClH:14].[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([C@H:22]([NH2:25])[CH2:23][CH3:24])=[CH:18][C:17]=1[CH3:26].[CH3:27]C(C)([O-])C.[Na+].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>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]>[Cl:14][C:11]1[C:6]([CH:4]([O:3][CH3:1])[O:5][CH3:27])=[CH:7][C:8]([NH:25][C@@H:22]([C:19]2[CH:20]=[CH:21][C:16]([Cl:15])=[C:17]([CH3:26])[CH:18]=2)[CH2:23][CH3:24])=[N:9][CH:10]=1

Komponenten

8

Edukt 4

HCID 634876Binap, (A+-)-HCID 2763069Ethyl 2-chloro-5-methylisonicotinateHCID 23676156Sodium t-butoxideHCID 57517333(R)-1-(4-chloro-3-methyl-phenyl)-propylamine hydrochloride

Produkt 1

HCID 67345901(5-Chloro-4-dimethoxymethyl-pyridin-2-yl)-[(R)-1-(4-chloro-3-methyl-phenyl)-propyl]-amine

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 2-chloro-5-methylpyridine-4-carboxylic acid ethyl ester (750 mg, 3.76 mmol), (R)-1-(4-chloro-3-methyl-phenyl)-propylamine hydrochloride (992 mg, 4.51 mmol) and sodium tert-butoxide (867 mg, 9.02 mmol) in degassed toluene (54 mL) was added Pd2(dba)3 (172 mg, 0.188 mmol) and BINAP (234 mg, 0.378 mmol) and the resulting mixture was stirred at 50° C. for 5 hours. The mixture was diluted with EtOAc, washed with saturated aqueous sodium bicarbonate, water and brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by flash chromatography on silica gel (cyclohexane/EtOAc) to give INT 54.

Aufarbeitung

  1. washwashed with saturated aqueous sodium bicarbonate, water and brine
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography on silica gel (cyclohexane/EtOAc)
  6. customto give INT 54

Quellen und Nachweise

ORD-Eintrag
ord-7b0497ee29e8451f99a9e00794603958
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08791100B2

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