Réaction #324406

Équation de réaction

5-[4-(tert-butyldimethylsilyloxy)phenyl]-3-(4-nitrophenyl)pyrazin-2-amine

5-[4-(tert-Butyldimethylsilyloxy)phenyl]-3-(4-nitrophenyl)pyrazin-2-amine

2-[4-(tert-butyldimethylsilyl oxy)phenyl]acetyl chloride

2-[4-(tert-butyldimethylsilyloxy)phenyl]acetyl chloride

water

→

Compound 11o

Rendement 48.1%

2-[4-(tert-Butyldimethylsilyloxy)phenyl]-N-[5-{4-(tert-butyldimethylsilyloxy)phenyl}-3-(4-nitrophenyl)pyrazin-2-yl]acetamide

Rendement 48.1%

Solvants

pyridine

Conditions de réaction

Traitement

1. 1
   Autreprepared above at 0° C.
2. 2
   Températurethe mixture was heated
3. 3
   TempératureAfter cooling to room temperature
4. 4
   Extractionthe product was extracted with ethyl acetate (100 mL×3)
5. 5
   ExtractionThe combined organic extract
6. 6
   Lavagewas washed successively with water (200 mL) and brine (200 mL)
7. 7
   Séchageby drying over anhydrous sodium sulfate
8. 8
   FiltrationAfter filtration and concentration under reduced pressure
9. 9
   Autrethe residue was purified by column chromatography (silica gel 50 g, n-hexane/ethyl acetate=2/1)

Mode opératoire

Under an argon atmosphere, to a mixture of 5-[4-(tert-butyldimethylsilyloxy)phenyl]-3-(4-nitrophenyl)pyrazin-2-amine (7o) (317 mg, 751 μmol) and 4-(dimethylamino)pyridine (15.3 mg, 125 μmol) dissolved in anhydrous pyridine (15 mL) was added 2-[4-(tert-butyldimethylsilyl oxy)phenyl]acetyl chloride (10) prepared above at 0° C. and the mixture was heated with stirring at 50° C. for 20 hours. After cooling to room temperature, to this was added water and the product was extracted with ethyl acetate (100 mL×3). The combined organic extract was washed successively with water (200 mL) and brine (200 mL), followed by drying over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the residue was purified by column chromatography (silica gel 50 g, n-hexane/ethyl acetate=2/1) to give Compound 11o (242 mg, 361 μmol, 48.1%) as a yellow solid. Rf=0.30 (n-hexane/ethyl acetate=2/1); 1H NMR (400 MHz, DMSO-d6) δ 0.15 (s, 6H), 0.20 (s, 6H), 0.92 (s, 9H), 0.93 (s, 9H), 3.44 (s, 2H), 6.67-6.74 (AA′BB′, 2H), 6.94-7.07 (2AA′BB′, 4H), 7.80-7.86 (AA′BB′, 2H), 8.01-8.12 (2AA′BB′, 4H), 9.05 (s, 1H), 10.85 (s, 1H); 13C NMR (67.8 MHz, DMSO-d6) δ −4.5 (2C), −4.6 (2C), 17.9, 18.0, 25.50 (3C), 25.51 (3C), 41.6, 119.4 (2C), 120.4 (2C), 123.2 (2C), 127.4, 128.2, 128.52 (2C), 128.54 (2C), 130.4 (2C), 138.7, 143.0, 144.5, 145.0, 146.9, 147.9, 153.9, 156.9, 168.9; IR (KBr, cm−1) 700, 741, 781, 839, 914, 1169, 1265, 1348, 1443, 1508, 1603, 1670, 2857, 2930, 2955.

Source