Potassium Carbonate → 5-[1-Biphenyl-4-ylmethyl-4,6-difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid methyl ester

HRID 1945296Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1945296
[C:1]1([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[C:12]3[CH:13]=[C:14]([F:28])[C:15]([C:18]4[CH:19]=[C:20]5[C:24](=[CH:25][CH:26]=4)[N:23]([CH3:27])[CH:22]=[CH:21]5)=[C:16]([F:17])[C:11]=3[N:10]=[C:9]2S(C)(=O)=O)=[CH:3][CH:2]=1.[CH3:39][O:40][C:41](=[O:50])[C:42]1[CH:47]=[C:46]([OH:48])[CH:45]=[CH:44][C:43]=1[CH3:49].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.CCOC(C)=O>[CH3:39][O:40][C:41](=[O:50])[C:42]1[CH:47]=[C:46]([O:48][C:9]2[N:8]([CH2:7][C:4]3[CH:5]=[CH:6][C:1]([C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)=[CH:2][CH:3]=3)[C:12]3[CH:13]=[C:14]([F:28])[C:15]([C:18]4[CH:19]=[C:20]5[C:24](=[CH:25][CH:26]=4)[N:23]([CH3:27])[CH:22]=[CH:21]5)=[C:16]([F:17])[C:11]=3[N:10]=2)[CH:45]=[CH:44][C:43]=1[CH3:49]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 13929055Methyl 5-hydroxy-2-methylbenzoateHCID 686594621-biphenyl-4-ylmethyl-4,6-difluoro-2-methanesulfonyl-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazole

Produkt 1

HCID 685739675-[1-Biphenyl-4-ylmethyl-4,6-difluoro-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazol-2-yloxy]-2-methyl-benzoic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A solution of 1-biphenyl-4-ylmethyl-4,6-difluoro-2-methanesulfonyl-5-(1-methyl-1H-indol-5-yl)-1H-benzoimidazole (1088 mg, 2.1 mmol), 5-hydroxy-2-methyl-benzoic acid methyl ester (513 mg, 3.1 mmol) and potassium carbonate (580 mg, 4.2 mmol) in DMF (20 mL) was stirred at room temperature under nitrogen. After 18 h, the reaction mixture was transferred to a microwave vial and heated under microwave at 130° C. for 10 min. The cooled reaction mixture was diluted with EtOAc and washed 3 times with saturated ammonium chloride, dried (MgSO4), filtered, and concentrated. Chromatography over silica gel afforded the desired product as a colorless foam.

Aufarbeitung

  1. customThe cooled reaction mixture
  2. washwashed 3 times with saturated ammonium chloride
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4a3e6e204c524f6db78196791ca3cb7e
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08394969B2

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