반응 #1908195

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N′-(3-cyano-4-isopropyloxyphenylcarbonyl)-4-bromo-2-methylbenzhydrazide

N′-(3-Cyano-4-isopropyloxyphenylcarbonyl)-4-bromo-2-methylbenzhydrazide

phosphorus oxychloride

→

title compound

수율 86.8%

2-(3-Cyano-4-isopropyloxyphenyl)-5-(4-bromo-2-methylphenyl)-1,3,4-oxadiazole

수율 86.8%

용매

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후처리

1. 1
   온도the heterogeneous reaction mixture was heated
2. 2
   온도to reflux for 6 h
3. 3
   추출extracted with EtOAc (2×150 mL)
4. 4
   건조The combined organic layers were dried with sodium sulfate and solvents
5. 5
   기타were removed under reduced pressure
6. 6
   기타The crude compound was purified by flash chromatography

실험 절차

In an oven-dried round bottom flask 145 mg (0.35 mmol) of N′-(3-cyano-4-isopropyloxyphenylcarbonyl)-4-bromo-2-methylbenzhydrazide (from EXAMPLE 87, Step A) was combined with 10 mL of anhydrous xylenes and 5 mL of phosphorus oxychloride and the heterogeneous reaction mixture was heated to reflux for 6 h. The resulting homogeneous mixture was cooled down to rt and combined with 200 mL of ice-water, neutralized to pH>10 and extracted with EtOAc (2×150 mL). The combined organic layers were dried with sodium sulfate and solvents were removed under reduced pressure. The crude compound was purified by flash chromatography using Biotage 40S (eluent: hexanes/EtOAc—4/1) to yield 121 mg of title compound: 1H NMR (500 MHZ, CDCl3) δ 1.50 (d, J=7.0, 6H), 2.78 (s, 3H), 4.80 (sep, J=7.0, 1H), 7.14 (d, J=9.0, 1H), 7.54 (dd, J=9.0, 2.0, 1H), 7.58 (d, J=2.0, 1H), 7.91 (d, J=8.5, 1H), 8.30 (d, J=2.0, 1H), 8.33 (dd, J=8.5, 2.0, 1H).

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