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Product Details of [ 259860-04-3 ]

CAS No. :259860-04-3
Formula : C8H5ClFN
M.W : 169.58
SMILES Code : FC1=C(Cl)C=CC2=C1NC=C2
MDL No. :MFCD12924614
InChI Key :OPEAQMMQYFSXKX-UHFFFAOYSA-N
Pubchem ID :22612745

Safety of [ 259860-04-3 ]

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 [ 259860-04-3 ]

* 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 [ 259860-04-3 ]

[ 259860-04-3 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 2106-49-2 ]
  • [ 1826-67-1 ]
  • [ 259860-04-3 ]
YieldReaction ConditionsOperation in experiment
11.4% In tetrahydrofuran; at -40 - 20℃; for 0.5h;Inert atmosphere; To a stirred solution of <strong>[2106-49-2]1-chloro-2-fluoro-3-nitrobenzene</strong> 1 (10.0 g, 56.98 mmol) in THF (100 mL) under inert atmosphere was added vinyl magnesium bromide (1M in THF solution; 170 mL, 170.94 mmol) at RT, cooled to -40 C and stirred for 30 mm. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with saturated NH4C1 solution (50 mL), extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with NH4C1 solution (40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. This was purified by silica gel chromatography using 2% EtOAc/ Hexanes to afford compound 2 (1.1 g, 11.4%) as a brown oil. 1H NMR (500 MHz, CDC13): (58.36 (br s, 1H), 7.31 (d, J = 8.0 Hz, 1H), 7.25-7.22 (m, 1H), 7.08-7.05 (m, 1H), 6.56-6.54 (m, 1H).
11.4% In tetrahydrofuran; at -40℃; for 0.5h;Inert atmosphere; Step 1: Synthesis of 6-chloro-7-fluoro-1H-indole (2):1003241 To a stirred solution of <strong>[2106-49-2]1-chloro-2-fluoro-3-nitrobenzene</strong> 1(10.0 g, 56.98 mmol) in THF (100 mL) under inert atmosphere was added vinyl magnesium bromide (1Mm THF solution; 170 mL, 170.94 mmol) at RT, cooled to -40 C and stirred for 30 mm. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with saturated NH4C1 solution (50 mL), extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with NH4C1 solution (40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. This was purified by silica gel column chromatography using 2% EtOAc/ Hexanes to afford compound 2 (1.1 g, 11.4%) as a brown oil. 1H NMR (500 MHz, CDC13): (58.36 (br s, 1H), 7.31 (d, J= 8.0 Hz, 1H), 7.25-7.22 (m, 1H),7.08-7.05 (m, 1H), 6.56-6.54 (m, 1H).
11.4% In tetrahydrofuran; at -40 - 20℃; for 0.5h;Inert atmosphere; Step 1: Synthesis of 6-chloro-7-fluoro-1H-indole (2) To a stirred solution of <strong>[2106-49-2]1-chloro-2-fluoro-3-nitrobenzene</strong> 1 (10.0 g, 56.98 mmol) in THF (100 mL) under inert atmosphere was added vinyl magnesium bromide (1M in THF solution; 170 mL, 170.94 mmol) at RT, cooled to -40 C. and stirred for 30 min. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with saturated NH4Cl solution (50 mL), extracted with EtOAc (2*50 mL). The combined organic extracts were washed with NH4Cl solution (40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. This was purified by silica gel column chromatography using 2% EtOAc/Hexanes to afford compound 2 (1.1 g, 11.4%) as a brown oil. 1H NMR (500 MHz, CDCl3): δ 8.36 (br s, 1H), 7.31 (d, J=8.0 Hz, 1H), 7.25-7.22 (m, 1H), 7.08-7.05 (m, 1H), 6.56-6.54 (m, 1H).
11.4% In tetrahydrofuran; at -40 - 20℃; for 0.5h;Inert atmosphere; To a stirred solution of <strong>[2106-49-2]1-chloro-2-fluoro-3-nitrobenzene</strong> 1 (10.0 g, 56.98 mmol) in THF (100 mL) under inert atmosphere was added vinyl magnesium bromide (1M in THF solution; 170 mL, 170.94 mmol) at RT, cooled to -40 C and stirred for 30 mm. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was quenched with saturated NH4C1 solution (50 mL), extracted with EtOAc (2 x 50 mL). The combined organic extracts were washed with NH4C1 solution (40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the cmde. This was purified by silica gel column chromatography using 2% EtOAc/ Hexanes to afford compound 2 (1.1 g, 11.4%) as a brown oil. 1H NMR (500 MHz, CDC13): 6 8.36 (br s, 111), 7.31 (d, J = 8.0 Hz, 1H), 7.25-7.22 (m, 1H),7.08-7.05 (m, 1H), 6.56-6.54 (m, 1H).of
In tetrahydrofuran; at -78℃; for 1h; To a solution of 1-chloro-2-fluoro-3-nitro-benzene (2.50 g, 14.2 mmol) in THF (50 ml) wasadded vinyl magnesium bromide (5.61 g, 42.7 mmol) at -78C and the reaction mixturewas stirred at same temperature for 1 h. Progress of the reaction was monitored by TLCand LCMS. After completion, the reaction mixture was quenched with saturated NH4CI(1 00 ml), diluted with H20 (400 ml) and extracted with EtOAc (500 ml). The organic10 layer was separated, dried over anhydrous Na2S04 and concentrated under vacuum. Thecrude obtained was purified by column chromatography (silica, 100-200 mesh, 5% EtOAcin hexanes) to afford afford 6-chloro-7-fluoro-1 H-indole Xl-5 (0.60 g) as a red liquid.Yield: 17%Basic LCMS Method 2 (ES-):168.00 (M-H)-, 66 % purity
In tetrahydrofuran; at 78℃; for 1h; To a solution of 1-chloro-2-fluoro-3-nitro-benzene (2.50 g, 14.2 mmol) in THF (50 mL) was added vinyl magnesium bromide (5.61 g, 42.7 mmol) at -78C and the reaction mixture was stirred at same temperature for 1h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was quenched with saturated NH4Cl (100 mL), diluted with H2O (400 mL) and extracted with EtOAc (500 mL). The organic layer was separated, dried over anhydrous Na2SO4 and concentrated under vacuum. The crude obtained was purified by column chromatography (silica, 100-200 mesh, 5% EtOAc in hexanes) to afford afford 6-chloro-7-fluoro-1H-indole XI-4 (0.60 g) as a red liquid. Yield: 17% Basic LCMS Method 2 (ES-): 168 (M-H)-, 66% purity.
In tetrahydrofuran; at -78℃; for 1h; To a solution of 1 -chloro-2-fluoro-3-nitro-benzene (2.50 g, 14.2 mmol) in THF (50 mL) was added vinyl magnesium bromide (5.61 g, 42.7 mmol) at -78 C and the reaction mixture was stirred at same temperature for 1 h. Progress of the reaction was monitored by TLC and LCMS. After completion, the reaction mixture was quenched with saturated NH4CI (100 mL), diluted with H20 (400 mL) and extracted with EtOAc (500 mL). The organic layer was separated, dried over anhydrous Na2S04 and concentrated under vacuum. The crude obtained was purified by column chromatography (silica, 100-200 mesh, 5% EtOAc in hexane) to afford afford 6-chloro-7-fluoro-1H-indole XI-3 (0.60 g) as a red liquid. (1022) Yield: 17% Basic LCMS Method 2 (ES ): 168.00 (M-H)-, 66 % purity.

 

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