Methyl chloroacetate → (2-{3-[(3,5-Bis-trifluoromethyl-benzoyl)-methyl-amino]-pyridin-4-yl}-5-fluoro-phenoxy)-acetic acid methyl ester

HRID 878027Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 878027
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]=[CH:12][N:11]=[CH:10][C:9]=2[N:14]([CH3:31])[C:15](=[O:30])[C:16]2[CH:21]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:19]=[C:18]([C:26]([F:29])([F:28])[F:27])[CH:17]=2)=[C:4]([OH:32])[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:40][C:41]([O:43][CH3:44])=[O:42]>CN(C=O)C.CCOC(C)=O>[CH3:44][O:43][C:41](=[O:42])[CH2:40][O:32][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[C:8]1[CH:13]=[CH:12][N:11]=[CH:10][C:9]=1[N:14]([C:15](=[O:30])[C:16]1[CH:17]=[C:18]([C:26]([F:27])([F:28])[F:29])[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=1)[CH3:31]

Komponenten

6

Edukt 3

HCID 7295Methyl chloroacetateHCID 11430Potassium CarbonateHCID 136209610N-[4-(4-Fluoro-2-hydroxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide

Produkt 1

HCID 86670700(2-{3-[(3,5-Bis-trifluoromethyl-benzoyl)-methyl-amino]-pyridin-4-yl}-5-fluoro-phenoxy)-acetic acid methyl esterAusbeute 57,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a solution of N-[4-(4-fluoro-2-hydroxy-phenyl)-pyridin-3-yl]-N-methyl-3,5-bis-trifluoromethyl-benzamide (150 mg, 0.327 mmol, example 48) in DMF (5 mL) was added K2CO3 (90 mg, 0.654 mmol) and methyl chloroacetate (0.06 mL, 0.654 mmol, CAS RN 96-34-4) at 25° C. and the resulting mixture was heated to 70° C. for 16 hours. The mixture was diluted with EtOAc (25 mL), washed with brine (10 mL), dried over anhydrous Na2SO4, filtered and evaporated in vacuo. The crude material thus obtained was purified by column chromatography over silica gel (30% EtOAc in n-hexane) to give 100 mg of the title compound. Pale yellow solid (58%). MS (ESI): m/z=531.0 [M+H]+.

Aufarbeitung

  1. washwashed with brine (10 mL)
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe crude material thus obtained
  6. customwas purified by column chromatography over silica gel (30% EtOAc in n-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c48cc906f7bf4822b1c4407018d05b8c
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987307B2

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