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[ CAS No. 866683-29-6 ] {[proInfo.proName]}

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Chemical Structure| 866683-29-6
Chemical Structure| 866683-29-6
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Product Details of [ 866683-29-6 ]

CAS No. :866683-29-6 MDL No. :MFCD23161611
Formula : C11H12N2Si Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 200.31 Pubchem ID :-
Synonyms :

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Application In Synthesis of [ 866683-29-6 ]

* 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 [ 866683-29-6 ]

[ 866683-29-6 ] Synthesis Path-Downstream   1~3

  • 1
  • [ 866683-29-6 ]
  • [ 146137-76-0 ]
  • [ 866683-74-1 ]
YieldReaction ConditionsOperation in experiment
45% With tetrabutyl ammonium fluoride; triethylamine In tetrahydrofuran at -78 - 60℃; for 2.16667h; 38 Combine 5-trimethylsilanylethynyl-nicotinonitrile (1. 30 g, 11. 5 mmol), (prepared as described in PREPARATION 3), 2-fluoro-5-iodobenzaldehyde (3. 45 g, 13. 8 mmol, (prepared essentially as described in Tet. Lett., 33, 7499, (1992)), bis (triphenylphosphine) palladium (II) dichloride (404 mg, 0. 575 mmol), copper (I) iodide (219 mg, 1. 15 mmol), and triethylamine (22. 4 mL, 161 mmol) in tetrahydrofuran (9 mL). Cool the suspension to-78 °C and treat with a 1. 0 M solution of tetrabutylammonium fluoride (11. 5 mL) in tetrahydrofuran. After 10 min, heat to 60 °C for 2 h. Cool to room temperature and filter through diatomaceous earth washing with ethyl acetate. Purify the crude product by silica gel chromatography, eluting with a gradient from 80 : 20 to 60 : 40 hexanes : ethyl acetate, to give the title compound as an off-white crystalline solid (1. 3 g, 45%). 1HNMR (400 MHz, DMSO-d6) 6 7. 51 (dd, J = 10. 5, 8. 8 Hz, 2H), 7. 93 (ddd, J = 8. 7, 4. 9, 2. 3 Hz, 1H), 8. 02 (dd, J = 6. 6, 2. 2 Hz, 1H), 8. 56 (t, J = 2. 2 Hz, 1H), 9. 01 (d, J = 2. 2 Hz, 1H), 9. 02 (d, J = 2. 2 Hz, 1H), 10. 16 (s, 1H) ; MS (ES) : 7n/z = 251. 0 [M-H]-.
Reference： [1]Current Patent Assignee: ELI LILLY & CO - WO2005/94822, 2005, A1 Location in patent: Page/Page column 43
  • 2
  • [ 866683-29-6 ]
  • [ 156150-67-3 ]
  • [ 866685-08-7 ]
YieldReaction ConditionsOperation in experiment
31% With tetrabutyl ammonium fluoride; triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at -78 - 70℃; Stir 5-trimethylsilanylethynyl-nicotinonitrile (300 mg, 1. 5 mmol), (prepared essentially as described in PREPARATION 3), <strong>[156150-67-3]2-chloro-1-fluoro-4-iodobenzene</strong> (390 mg, 1. 5 mmol), bis (triphenylphosphine) palladium (II) dichloride (50 mg, 0. 08 mmol) and copper (I) iodide (20 mg, 0. 15 mmol) in triethylamine (15 mL) under nitrogen and cool to - 78C. Add a 1 M solution of tetrabutylammonium fluoride (1. 5 mL) in tetrahydrofuran and warm to room temperature and then heat at 70 C until complete by thin layer chromatography. Concentrate and purify the residue by silica gel chromatography, eluting with hexanes : ethyl acetate, and then recrystallize from hexanes : ethyl acetate to give the title compound (120 mg, 31%). 1H NMR (400 MHz, CDCl3) 6 7. 18 (t, J = 8. 8 Hz, 1H), 7. 46-7. 42 (m, 1H), 7. 62 (dd, J = 6. 8 Hz, 2. 0 Hz, 1H), 8. 06 (t, J = 2. 2 Hz, 1H), 8. 82 (d, J = 1. 8 Hz, 1H), 8. 91 (d, J = 2. 2 Hz, 1H) ; HRMS calcd for C14H7ClFN2 257. 0282. Found 257. 0266 ; Anal. Calcd for C14H6ClFN2 : C, 65. 52 ; H, 2. 37 ; N, 10. 91. Found : C, 65. 59 ; H, 2. 48 ; N, 10. 67.
Reference： [1]Patent: WO2005/94822,2005,A1 .Location in patent: Page/Page column 78
  • 3
  • [ 122918-25-6 ]
  • [ 866683-29-6 ]
  • [ 1380072-64-9 ]
Reference： [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 544 - 549

Tags: 866683-29-6; 5-[2-(Trimethylsilyl)ethynyl]pyridine-3-carbonitrile;

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