Dimethylformamide → 2-{3-[2-(3-Cyanophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoic Acid

HRID 1168454

Reaktionsgleichung

Reaktionsgleichung von HRID 1168454
Br[C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:33])=[C:11]([CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH:17]([O:21][CH2:22][C:23]4[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:24]=4[C:25]([OH:27])=[O:26])[CH2:16]3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1.[CH3:34][N:35](C)C=O>[C-]#N.[Zn+2].[C-]#N>[C:34]([C:2]1[CH:3]=[C:4]([C:8]2[O:9][C:10]([CH3:33])=[C:11]([CH2:13][O:14][CH:15]3[CH2:20][CH2:19][CH2:18][CH:17]([O:21][CH2:22][C:23]4[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[C:24]=4[C:25]([OH:27])=[O:26])[CH2:16]3)[N:12]=2)[CH:5]=[CH:6][CH:7]=1)#[N:35]

Komponenten

4

Edukt 2

HCID 6228DimethylformamideHCID 224936532-{3-(2-(3-Bromophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoic acid

Produkt 1

HCID 224936902-{3-[2-(3-Cyanophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

13 mg of 2-{3-[2-(3-bromophenyl)-5-methyloxazol-4-ylmethoxy]cyclohexyloxymethyl}-6-methylbenzoic acid and 25 mg of zinc cyanide were dissolved in 5 ml of dimethylformamide. The reaction mixture was degassed and charged with argon, and 20 mg of tetrakistriphenylphosphinepalladium were added. The mixture was stirred at 100° C. for 12 hours. After cooling to room temperature, water was added to the reaction mixture, which was then extracted with ethyl acetate. The combined organic phases were dried over magnesium sulfate, the solvents were removed under reduced pressure and the residue was purified by RP-HPLC. This gave 68 as an amorphous light-yellow solid. C27H28N2O5 (460.53), MS(ESI): 461.20 (M+H+).

Aufarbeitung

  1. customThe reaction mixture was degassed
  2. additioncharged with argon, and 20 mg of tetrakistriphenylphosphinepalladium
  3. additionwere added
  4. temperatureAfter cooling to room temperature
  5. additionwater was added to the reaction mixture, which
  6. extractionwas then extracted with ethyl acetate
  7. dry with materialThe combined organic phases were dried over magnesium sulfate
  8. customthe solvents were removed under reduced pressure
  9. customthe residue was purified by RP-HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5a278800554141c4a2e5ada83e3441ae
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06624185B2

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