Potassium Phosphate, Tribasic → 4-(2-Chloropyridine-3-yl)-1-(triisopropylsilyl)-1h-pyrrolo[2,3,b]pyridine

HRID 227742

반응식

HRID 227742 반응식
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]2[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:14])[CH3:13])[CH:9]=[CH:10][C:3]=12.[Cl:21][C:22]1[C:27](B(O)O)=[CH:26][CH:25]=[CH:24][N:23]=1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:21][C:22]1[C:27]([C:2]2[CH:7]=[CH:6][N:5]=[C:4]3[N:8]([Si:11]([CH:18]([CH3:20])[CH3:19])([CH:15]([CH3:17])[CH3:16])[CH:12]([CH3:13])[CH3:14])[CH:9]=[CH:10][C:3]=23)=[CH:26][CH:25]=[CH:24][N:23]=1

참가 물질

6

반응물 4

HCID 62657Potassium Phosphate, TribasicHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 2762704(2-Chloropyridin-3-yl)boronic acidHCID 114382724-Chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

생성물 1

HCID 577562484-(2-Chloropyridine-3-yl)-1-(triisopropylsilyl)-1h-pyrrolo[2,3,b]pyridine

시약·촉매·용매 1

HCID 167845palladium(II) acetate촉매

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).

후처리

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

출처 및 근거

ORD 기록
ord-9535f71b09da416db080e6d2898bf7a8
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560551B2

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