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Chemical Structure| 5326-34-1 Chemical Structure| 5326-34-1

Structure of 5326-34-1

Chemical Structure| 5326-34-1

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Product Details of [ 5326-34-1 ]

CAS No. :5326-34-1
Formula : C7H6BrNO2
M.W : 216.03
SMILES Code : C1=C([N+]([O-])=O)C(=CC=C1C)Br
MDL No. :MFCD00024180
InChI Key :UPBUTKQMDPHQAQ-UHFFFAOYSA-N
Pubchem ID :79224

Safety of [ 5326-34-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 5326-34-1 ]

* 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 [ 5326-34-1 ]

[ 5326-34-1 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 5326-34-1 ]
  • [ 1826-67-1 ]
  • [ 165669-07-8 ]
YieldReaction ConditionsOperation in experiment
42% In tetrahydrofuran; at -60 - -30℃; for 1h;Inert atmosphere; To a solution of 1-bromo-4-methyl-2-nitro-benzene (40.0 g, 185 mmol, 25.3 mL) in tetrahydrofuran (400 mL) was added bromo(vinyl)magnesium (1 M, 611 mL) at -60 OC under nitrogen gas atmosphere. The reaction mixture was then stirred at -30 OC for 1 hour. On completion, the reaction mixture was quenched with saturated ammonium chloride solution (150 mL), followed with water (100 mL). The mixture was concentrated in vacuo to remove the tetrahydrofuran. The residue was extracted with ethyl acetate (2×500 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was then purified by column chromatography (petroleum ether:ethyl acetate=100:1) to give the title compound (18.0 g, 42% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) delta 11.27 (br s, 1H), 7.37 (t, J=2.8 Hz, 1H), 7.18 (d, J=7.6 Hz, 1H), 6.75 (dd, J=0.8, 7.6 Hz, 1H), 6.57 (dd, J=1.6, 3.2 Hz, 1H), 2.44 (s, 3H).
With ammonium chloride; In tetrahydrofuran; ethyl acetate; Production Example 7 7-Bromo-4-methyl-1H-indole To 300 ml of a solution of 65.0 g (301 mmol) of 2-bromo-5-methylnitrobenzene in tetrahydrofuran was added 1 liter of a 1.0M solution of vinyl magnesium bromide (1 mol) in tetrahydrofuran at -60 C. in a nitrogen atmosphere under stirring during 1 hour. To the reaction mixed solution were added a saturated aqueous solution of ammonium chloride and ethyl acetate, and the resulting insoluble matters were filtered off. The resulting filtrate was dried over magnesium sulfate, concentrated, and then the resulting residue was purified by a silica gel column chromatography to give 35.5 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm); 2.42(3H,s), 6.55(1H,s) 6.73(1H,d,J=7.6 Hz), 7.16(1H,d,J=7.6 Hz), 7.35(1H,s), 1 11.24(1H,brs)
With ammonium chloride; In tetrahydrofuran; ethyl acetate; PRODUCTION EXAMPLE 7 7-Bromo-4-methyl-1H-indole 1 l (1 mol) of a tetrahydrofuran solution containing 1.0 M vinylmagnesium bromide was added to a tetrahydrofuran solution (300 ml) containing 65.0 g (301 mmol) of 2-bromo-5-methylnitrobenzene at -60 C. under stirring for one hour in nitrogen atmosphere. An aqueous saturated ammonium chloride and ethyl acetate were added to the reaction mixture solution, and the insoluble matters were filtered off. The filtrate was dried over magnesium sulfate and concentrated. Then, the residue was purified by silica gel column chromatography, to give 35.5 g of the title compound. 1H-NMR(DMSO-d6) delta (ppm): 2.42(3H, s), 6.55(1H, s), 6.73(1H, d, J=7.6 Hz), 7.16(1H, d, J=7.6 Hz), 7.35(1H, s), 11.24(1H, br s)
In tetrahydrofuran; at -50℃; for 1.5h; (4-methyl-1 H-indol-7-yl)(phenyl)methanamine - To a solution of 1 -bromo-4-methyl-2-nitrobenzene (2.0 g, 9.26 mmol) in THF was added vinyl magnesium bromide 1 M in THF (27.8 ml_, 27.77 mmol) at - 50C. The reaction was finished after 1 h30. The reaction was quenched with sat. NH4CI. The aqueous layer was extracted with a non-water miscible organic solvent. The combined organic layers were dried over MgS04, filtered and the solution was concentrated to dryness. The crude material was purified on silica gel column chromatography usinf hexanes/EtOAc (9:1 ) as eluent. A solution of the freshly synthesized 7-bromo-4-methyl-1 H-indole (1 .1 g, 5.24 mmol), zinc cyanide (860 mg, 7.32 mmol) and Pd(PPh3)4 (0.03 eq.) in DMF Ex.97 was heated under microwave irradiation at 170C for 1 h. After cooling, water was added to quench the reaction. The aqueous layer was extracted with a non-water miscible organic solvent. The combined organic layers were dried over MgS04, filtered and the solution was concentrated under reduced pressure. The crude material was purified on silica gel column chromatography using hexanes/EtOAc (12:1 to 4:1 ) as eluent. The titled compound was then obtained following the modified procedure described in WO2006035157 (Protocol A) - Yield: 2% ; appearance: pale brown solid ; 1 H NMR, d (ppm) (Methanol d4) : 2.49 (s, 3H); 5.51 (s, 1 H); 6.47 (d, 1 H, J=3.2Hz); 6.81 (dd, 1 H, J=0.6Hz , J=7.3Hz); 7.01 (d, 1 H, J=7.3Hz); 7.17-7.22 (m, 2H); 7.25-7.31 (m, 2H); 7.39- 7.43 (m, 2H)

 

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