Triethylamine → 2-(benzyloxy)-N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)benzamide

HRID 1946580Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1946580
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.[Cl:24][C:25]1[C:30]([NH2:31])=[CH:29][CH:28]=[C:27]([C:32]([F:35])([F:34])[F:33])[N:26]=1.C(N(CC)CC)C>C1COCC1.CN(C=O)C.C1(C)C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH:31][C:30]1[C:25]([Cl:24])=[N:26][C:27]([C:32]([F:34])([F:33])[F:35])=[CH:28][CH:29]=1)=[O:13])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

8

Edukt 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18105812-Benzyloxybenzoic acidHCID 27376462-Chloro-6-(trifluoromethyl)pyridin-3-amine

Produkt 1

HCID 597836062-(benzyloxy)-N-(2-chloro-6-(trifluoromethyl)pyridin-3-yl)benzamideAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideKatalysatorHCID 1140TolueneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a stirring solution of 2-(benzyloxy)benzoic acid (2.55 g, 11.19 mmol) and oxalyl chloride (2.84 g, 22.39 mmol) in THF (20 mL) was added a few drops of DMF (0.012 mL, 0.153 mmol) at 0° C. The reaction mixture was allowed to warm to room temperature and further stirred 30 minutes, diluted with toluene and then solvent evaporated. The residue was taken up in THF (20 mL) and to this solution was added 2-chloro-6-(trifluoromethyl)pyridin-3-amine (2.0 g, 10.18 mmol) at 0° C. followed by the addition of triethylamine (4.68 mL, 33.6 mmol). The reaction mixture was allowed to stir 3 days at room temperature then quenched with saturated bicarbonate solution, extracted with EtOAc and solvent evaporated to afford title compound 72 (3.0 g, 73% yield) after purification by flash chromatography (0 to 100% ethyl acetate in hexane). LRMS (ESI): (calc) 406.07 (found) 407.4 (MH)+.

Aufarbeitung

  1. customsolvent evaporated
  2. customthen quenched with saturated bicarbonate solution
  3. extractionextracted with EtOAc and solvent
  4. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-6445b47fa3ca4492a02727469ffcd765
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399452B2

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