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4-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

2-chlorpyridine-3-boronic acid

2-(dicyclohexylphosphino)biphenyl

K3PO4

→

4-(2-chloropyridine-3-yl)-1-(triisopropylsilyl)-1H -pyrrolo[2,3,b]pyridine

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후처리

1. 1
   기타The tube was purged with argon for 5 minutes
2. 2
   workup.ADDITIONDioxane (30 mL) was added via syringe under a positive argon flow
3. 3
   기타The tube was sealed
4. 4
   workup.WAITThen the tube was placed in a preheated oil bath at 110° C. for 2 h
5. 5
   온도The reaction was cooled down to room temperature
6. 6
   여과The content was filtered through a plug of celite with an aid of diethyl ether
7. 7
   농축The filtrated was concentrated under reduced pressure
8. 8
   기타The product was purified by column chromatography
9. 9
   workup.ADDITIONa mixture of 95:5 Hex

실험 절차

4-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine (5.03 g, 16.3 mmol, 1 equiv), 2-chlorpyridine-3-boronic acid (4.36 g, 27.7 mmol, 1.7 equiv), palladium acetate (183 mg, 0.815 mmol, 5 mol %), 2-(dicyclohexylphosphino)biphenyl (571 mg, 1.63 mmol, 10 mol %), and finely ground anhydrous K3PO4 (10.4 g, 48.9 mmol, 3 equiv) were added into a sealed tube. The tube was purged with argon for 5 minutes. Dioxane (30 mL) was added via syringe under a positive argon flow. The tube was sealed and the reaction was stirred at RT for 5 minutes. Then the tube was placed in a preheated oil bath at 110° C. for 2 h. The reaction was cooled down to room temperature. The content was filtered through a plug of celite with an aid of diethyl ether. The filtrated was concentrated under reduced pressure. The product was purified by column chromatography using a mixture of 95:5 Hex:Et2O as eluent. The product, 4-(2-chloropyridine-3-yl)-1-(triisopropylsilyl)-1H -pyrrolo[2,3,b]pyridine was obtained as a light yellow solid. 1H NMR (Varian, 300 MHz, CDCl3) ppm: 8.35 (d, J=4.7 Hz, 1H), 8.30−8.28 (m, 1H), 8.10−8.03 (m, 1H), 7.40−7.30 (m, 2H), 7.15 (dd, J=4.3, 1.7 Hz, 1H), 6.54 (dd, J=3.6, 1.9 Hz, 1H), 1.89 (sept, J=7.4 Hz, 3H), 1.15 (d, J=7.4 Hz, 18H).

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