Reaktion #69406

Reaktionsgleichung

N′,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide

4-ethoxy-3-(trifluoromethyl)benzoic acid

HOBt

EDCI

NaCl

→

4-(5-(4-isopropoxy-3-(trifluoromethyl)phenyl)-1,2,4-oxadiazol-3-yl)-2,3-dihydro-1H-inden-1-ol

Ausbeute 63.0%

Lösungsmittel

DMF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction was stirred for additional 30 min at room temperature
2. 2
   workup.ADDITIONThe reaction was diluted
3. 3
   Extraktionextracted with EtOAc (80 ml×3)
4. 4
   TrocknenThe organic phase was dried over Na2SO4 anhydrous
5. 5
   Einengenconcentrated under reduced pressure
6. 6
   SonstigeThe product was purified by column chromatography

Vorschrift

In a microwave vial, a stirring solution of 4-ethoxy-3-(trifluoromethyl)benzoic acid (200 mg, 0.97 mmol) in DMF was treated with HOBt (172 mg, 1.26 mmol) and EDCI (242 mg, 1.26 mmol) at room temperature. The reaction was stirred for 20 min followed by addition, in a single portion, of N′,1-dihydroxy-2,3-dihydro-1H-indene-4-carboximidamide (243 mg, 1.26 mmol). The reaction was stirred for additional 30 min at room temperature and then heated to 130° C. for 35 min in the initiator. The reaction was diluted using a saturated solution of NaCl and extracted with EtOAc (80 ml×3). The organic phase was dried over Na2SO4 anhydrous and concentrated under reduced pressure. The product was purified by column chromatography using CH2Cl2:MeOH (9:1) to offer the product as pale yellow solid in 63% yield (229 mg).

Quelle