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Chemical Structure| 769-56-2 Chemical Structure| 769-56-2

Structure of 769-56-2

Chemical Structure| 769-56-2

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Product Details of [ 769-56-2 ]

CAS No. :769-56-2
Formula : C6H2Br2N2O
M.W : 277.90
SMILES Code : BrC1=CC2=NON=C2C(Br)=C1
MDL No. :MFCD02114624

Safety of [ 769-56-2 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Application In Synthesis of [ 769-56-2 ]

* 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 [ 769-56-2 ]

[ 769-56-2 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 769-56-2 ]
  • [ 144163-68-8 ]
  • [ 1569653-80-0 ]
YieldReaction ConditionsOperation in experiment
14% With N-ethyl-N,N-diisopropylamine; In 1-methyl-pyrrolidin-2-one; at 100℃;Inert atmosphere; Sealed tube; 4,6-dibromobenzo[c][l ,2,5]oxadiazole (1.1509 g, 4.14 mmol) and N-methyl-l-(thiazol-2- yl)methanamine (4.97 mmol) were massed into a tube. The tube was evacuated and flushed with argon for three cycles. NMP (6 mL) and DIPEA (0.94 mL, 5.38 mmol) were then added and the tube was sealed and heated to 100 C overnight. Upon cooling to room temperature the mixture was diluted with water and EtOAc. The layers were separated and the aqueous layer was back- extracted with EtOAc. The combined organic layers were then washed with water (5x), brine, dried (Na2S04), filtered and concentrated to give an oil. The crude oil was then purified via flash column chromatography (30 % EtOAc / hexane) to afford 0.1872 g (14 % yield) of aniline. This aniline (0.1872 g, 0.58 mmol) and 3-formylphenylboronic acid (0.0899 g, 0.60 mmol) were massed into a tube. The tube was evacuated and purged with argon (3x). DME (1.5 mL) and 2M Na2C03 (0.9 mL, 1.74 mmol) were then added followed by Pd(PPh3)4 (0.0335 g, 0.029 mmol). The tube was then sealed and heated to 85 C overnight. Upon cooling to room temperature the mixture was diluted with water and EtOAc. The layers were separated and the aqueous layer was back-extracted with EtOAc. The combined organic layers were then washed with water (5x), brine, dried (Na2S04), filtered and concentrated to give an oil. This crude oil was then dissolved in THF (4 mL) and cooled to 0 C. CF3TMS (0.17 mL, 1.16 mmol) was added followed by TBAF (0.06 mL, 1.0 M solution in THF). The reaction was then stirred for 60 minutes before re- cooling to 0C and 4N HC1 (aq) was added and stirred for 60 minutes. The mixture was diluted with water and EtOAc. The layers were separated and the aqueous layer was basified. The aqueous layer was then re-extracted with EtOAc. The combined organic layers were was with water, brine, dried (Na2S04), filtered and concentrated to give a crude oil. This material was purified via flash column chromatography with step-gradient (100 % DCM to 0.5 % MeOH / DCM) to afford 0.0339 g (14 % yield, 3 steps) of TRV-1459. *H NMR (CDC13, 700 MHz) δ = 7.77 (d, J = 3.2 Hz, 1H), 7.73 (s, 1H), 7.66 (dt, J = 7.2, 1.6 Hz, 1H), 7.55-7.51 (m, 2H), 7.31 (s, 1H), 7.30 (d, J = 3.2 Hz, 1H), 6.46 (s, 1H), 5.46 (s, 2H), 5.13 (q, J = 6.6 Hz, 1H), 3.32 (s, 3H).
 

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