Sodium borohydride → 2-(3-(aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

HRID 1428704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1428704
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]2[C:15]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)=[N:16][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:18][CH:19]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1)#[N:2].[BH4-].[Na+]>C(O)C.C(OCC)(=O)C.[NiH6-5]Cl>[NH2:2][CH2:1][C:3]1[CH:4]=[C:5]([CH:9]([CH3:31])[C:10]([NH:12][CH2:13][C:14]2[C:15]([C:24]3[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=3)=[N:16][C:17]([C:20]([F:23])([F:21])[F:22])=[CH:18][CH:19]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1

Komponenten

6

Edukt 2

HCID 4311764Sodium borohydrideHCID 866802072-(3-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide

Produkt 1

HCID 866802092-(3-(aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamideAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178479586HCID 178479586, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a stirred solution of 2-(3-cyanophenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (217 mg, 5.13 mmol) in dry ethanol (15 mL), cooled to 0° C., were added nickel(II) chloride hexahydride (121 mg, 5.13 mmol). Sodium borohydride (136 mg, 35.9 mmol) was added in small portions over 10 min. The reaction mixture was allowed to warm to room temperature and left to stir for a further 1 h. The purple residue was dissolved in ethyl acetate (50 mL) and extracted with saturated NaHCO3. The organic layer was dried over magnesium sulfate and the solvent removed in vacuo to yield 2-(3-(aminomethyl)phenyl)-N-((2-m-tolyl-6-(trifluoromethyl)pyridin-3-yl)methyl)propanamide (130 mg, 60%).

Aufarbeitung

  1. waitleft
  2. extractionextracted with saturated NaHCO3
  3. dry with materialThe organic layer was dried over magnesium sulfate
  4. customthe solvent removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fd06d700d42048d08cb6d2ac88a9555a
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08937092B2

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