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Chemical Structure| 640735-25-7 Chemical Structure| 640735-25-7
Chemical Structure| 640735-25-7

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

CAS No.: 640735-25-7

4.5 *For Research Use Only !

Cat. No.: A394058 Purity: 97%

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Product Details of [ 640735-25-7 ]

CAS No. :640735-25-7
Formula : C16H25FN2Si
M.W : 292.47
SMILES Code : CC([Si](N1C=CC2=C(F)C=CN=C21)(C(C)C)C(C)C)C
MDL No. :MFCD11616419
InChI Key :YESANHMKGXGZLQ-UHFFFAOYSA-N
Pubchem ID :11266334

Safety of [ 640735-25-7 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338

Application In Synthesis of [ 640735-25-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 640735-25-7 ]

[ 640735-25-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 640735-25-7 ]
  • [ 640735-23-5 ]
YieldReaction ConditionsOperation in experiment
94% With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 0 - 20℃; for 1h;Inert atmosphere; [0722] To a stirred solution of 4-fluoro-i-(triisopropylsilyl)-1H-pyrrolo [2,3-bj pyridine (3 g, 10 mmol) in THF (15 mL) at 0 C under an argon atmosphere was added tetra butyl ammonium fluoride 1M in THF (10.5 mL). The reaction mixture was warmed to room temperature and stirred for 1 h. After consumption of starting material (by TLC), the reactionmixture was diluted with water (50 mL) and extracted with EtOAc (2 x 100 mL). The combined organic extracts were dried over sodium sulfate, filtered and concentrated in vacuo. The crude material was purified by column chromatography using 20%EtOAc: Hexane to afford 4-fluoro-1H-pyrrolo [2,3-bj pyridine (1.3 g, 94%) as an off-white solid. ?H NMR (CDC13, 400 MHz): 10.52 (brs, 1H), 8.30-8.25 (m, 1H), 7.32-7.30 (m, 1H), 6.81 (dd, 1H), 6.59 (s, 1H); TLC: 20% EtOAc Hexane (R 0.2).
  • 2
  • [ 319474-34-5 ]
  • [ 640735-25-7 ]
  • 3
  • [ 640735-25-7 ]
  • [ 5654-97-7 ]
  • [ 956460-93-8 ]
  • 4
  • [ 13154-24-0 ]
  • [ 640735-23-5 ]
  • [ 640735-25-7 ]
YieldReaction ConditionsOperation in experiment
68% To a suspension of sodium hydride (60% dispersion in mineral oil, 2.14 g, 53.5 mmol) in dry N,N-dimethylformamide (30 mL) was added a solution of <strong>[640735-23-5]4-fluoro-1H-pyrrolo[2,3-b]pyridine</strong> (5.77 g, 42.46 mmol) in dry N,N-dimethylformamide (58 mL) dropwise at 0 C. The mixture was stirred at 0 C for 15 min. To the mixture was added a solution of triisopropylsilyl chloride (10 mL, 46.71 mmol) in dry N,N-dimethylformamide (12 mL) dropwise at 0 C over 30 min. The reaction mixture was allowed to warm to room temperature and the mixture was stirred at room temperature for 42 h. The reaction mixture was poured into ice water (800 mL) and the mixture was extracted with dichloromethane (4 x 200 mL). The combined organic layers were washed with water (2 x 200 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by gradient silica gel column chromatography eluting with n-heptane:ethyl acetate (100:0 to 50:50) to afford the title compound (8.51 g, 29.14 mmol, 68%) as a pale yellow liquid. LCMS Method A: 99%, tR=2.242 min, m/z = 293.2 [M+H]+.
 

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