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[ CAS No. 1147014-68-3 ] {[proInfo.proName]}

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Chemical Structure| 1147014-68-3
Chemical Structure| 1147014-68-3
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Product Details of [ 1147014-68-3 ]

CAS No. :1147014-68-3 MDL No. :MFCD16877440
Formula : C11H13N3Si Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 215.33 Pubchem ID :-
Synonyms :

Safety of [ 1147014-68-3 ]

Signal Word: Class:
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Application In Synthesis of [ 1147014-68-3 ]

* 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 [ 1147014-68-3 ]

[ 1147014-68-3 ] Synthesis Path-Downstream   1~6

  • 1
  • [ 3680-69-1 ]
  • [ 1066-54-2 ]
  • [ 1147014-68-3 ]
YieldReaction ConditionsOperation in experiment
64% With triethylamine In N,N-dimethyl-formamide at 110℃; for 3h; 31 A mixture of 4-chloro-7H-pyrrolo[2,3-d]pyrimidine (10 g, 65 mmol), ethynyl- trimethyl-silane (9.5 g, 97 mmol), PdCl2(PPh3)2 (4.56 g, 6.5 mmol), CuI (1.2 g, 6.5 mmol) and TEA (195 mL) were suspended in anhydrous DMF (38 mL) and heated at 110 0C for 3 h. The reaction mixture was filtered while still hot and concentrated in vacuo. Resulting residue was taken up in EtOAc (100 mL) and washed with water and brine. Organic phase was evaporated and purified on silica gel column to afford the desired product as a beige solid (9 g, 64%).
Reference： [1]Current Patent Assignee: SANOFI - WO2009/55674, 2009, A1 Location in patent: Page/Page column 53
  • 2
  • [ 1147014-68-3 ]
  • [ 701-07-5 ]
  • [ 1147014-80-9 ]
YieldReaction ConditionsOperation in experiment
6% With tetrabutyl ammonium fluoride;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 140℃; for 0.25h;Microwave irradiation; A mixture of 14 (0.114 g, 0.53 mmol), 19 (0.171 g, 0.79 mmol), PdCl2(PPh3)2 (0.037 g, 0.053 mmol) and TBAF (IM in THF) (2.65 mL, 2.65 mmol) were suspended in anhydrous THF (1 mL) and microwaved at 140 0C for 15 min. The reaction mixture was cooled to room temperature and diluted with DCM (30 mL). The mixture was filtered and concentrated in vacuo. The crude product was purified by HPLC to afford the title compound (0.09 g, 6%).[0209] 1H NMR (500 MHz, DMSO-J6): delta 1.37 (d, J = 6.1 Hz, 6H), 4.75-4.80 (m, IH), 6.67 (d, J = 3.5 Hz, IH), 7.01 (t, J = 7.4 Hz, IH), 7.17 (d, J = 8.4 Hz, IH), 7.44-7.47 (m, IH), 7.61- 7.63 (m, IH), 7.69 (d, J = 3.5 Hz, IH ), 8.75 (s, IH), 12.3 (s, IH)[0210] MS (ES+): m/z 278 (M+H)+
Reference： [1]Patent: WO2009/55674,2009,A1 .Location in patent: Page/Page column 59-60
  • 3
  • [ 1147014-68-3 ]
  • [ 65232-57-7 ]
  • [ 1147014-82-1 ]
YieldReaction ConditionsOperation in experiment
15% With tetrabutyl ammonium fluoride In tetrahydrofuran at 160℃; for 0.25h; Microwave irradiation; 45 A mixture of 14 (0.1474 g, 0.684 mmol), 2-bromo-l,3-diethyl-benzene (0.218 g, 1.03 mmol), PdCl2(PPh3)2 (0.048 g, 0.068 mmol) and TBAF (IM in TηF) (2 mL, 2 mmol) were suspended in anhydrous TηF (1 mL) and microwaved at 160 0C for 15 min. The reaction mixture was cooled to room temperature and diluted with DCM (30 mL). The mixture was filtered and concentrated in vacuo. The crude product was purified by column chromatography to afford the title compound (0.028 g, 15%).[0215] 1H NMR (500 MHz, DMSO-J6): δ 1.28 (d, J = 7.5 Hz, 6H), 2.94 (q, J = 7.6 Hz, 4H), 6.61-6.62 (m, IH), 7.23 (d, J = 7.7 Hz, 2H), 7.35-7.38 (m, IH), 7.70-7.71 (m, IH), 8.78 (s, IH), 12.3 (s, IH)[0216] MS (ES+): m/z 276 (M+H)+
Reference： [1]Current Patent Assignee: SANOFI - WO2009/55674, 2009, A1 Location in patent: Page/Page column 61
  • 4
  • [ 1147014-68-3 ]
  • [ 101980-41-0 ]
  • [ 1147014-94-5 ]
YieldReaction ConditionsOperation in experiment
16% With tetrabutyl ammonium fluoride; triethylamine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In N,N-dimethyl-formamide; at 140.0℃; for 1.0h;Microwave irradiation; Argon was bubbled into a solution of 14 (200 mg, 0.93 mmol), 28 (226 mg, 0.93 mmol), PdCl2(PPrIs)2 (133 mg, 0.19 mmol), cuprous iodide (38 mg, 0.2 mmol), triethylamine (1 mL), tetrabutylammoniumfluoride (243 mg, 0.93 mmol) in dimethyl formamide (7 mL) for 5 min. The reaction vessel was sealed and heated at 1400C for 60 min in a microwave reactor. The reaction mixture was cooled, concentrated under reduced pressure, diluted with ethyl acetate (100 mL), filtered, concentrated and purified on preparative etaPLC to give the title compound as a yellow solid (45 mg, 16%).[0246] 1H NMR (500 MHz, DMSO-J6): delta 1.36 (d, J= 6.9 Hz, 6H), 3.63-3.69 (m, IH), 6.77 (dd, J = 3.4, 1.6 Hz, IH), 7.73-7.78 (m, 2H), 8.30 (dd, J = 8.7, 2.4 Hz, IH), 8.50 (d, J= 2.5 Hz, IH), 8.81 (s, IH), 12.45 (s, IH) [0247] MS (ES+): m/z 307 (M+H)+
Reference： [1]Patent: WO2009/55674,2009,A1 .Location in patent: Page/Page column 70
  • 5
  • [ 1147014-97-8 ]
  • [ 1147014-68-3 ]
  • [ 1147014-98-9 ]
YieldReaction ConditionsOperation in experiment
16% With tetrabutyl ammonium fluoride;bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 160℃; for 0.25h;Microwave irradiation; A mixture of 14 (182 mg, 0.85 mmol), 31 (182 mg, 0.56 mmol), Pd(PPh3)4Cl2 (40 mg, 0.06 mmol), and IM TBAF in TetaF (3.5 mL, 3.5 mmol) was irradiated in the microwave at 160 0C for 15 min. The solids were filtered, the filtrate was concentrated in vacuo, and the residue purified by etaPLC. The fractions were neutralized with sat NaHCO3 and extracted with EtOAc. The organic layers were concentrated in vacuo to afford the title compound as a yellow-brown solid (30 mg, 16%).[0259] 1H NMR (500 MHz, DMSO-J6) delta 1.32 (d, J= 6.9 Hz, 6H), 3.53 (qn, J= 6.8 Hz, IH), 6.66 (d, J = 3.4 Hz, IH), 7.53 (dd, J = 8.3, 1.7 Hz, IH), 7.62-7.67 (m, 2H), 7.71 (d, J = 3.4 Hz, IH), 8.77 (s, IH)[0260] MS (ES+): m/z 340/342 (M+H)+
Reference： [1]Patent: WO2009/55674,2009,A1 .Location in patent: Page/Page column 73
  • 6
  • [ 1100318-96-4 ]
  • [ 1066-54-2 ]
  • [ 1147014-68-3 ]
Reference： [1]ACS Combinatorial Science,2015,vol. 17,p. 5 - 10

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