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Chemical Structure| 1262985-25-0 Chemical Structure| 1262985-25-0

Structure of 1262985-25-0

Chemical Structure| 1262985-25-0

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Product Details of [ 1262985-25-0 ]

CAS No. :1262985-25-0
Formula : C10H11BrN2O
M.W : 255.11
SMILES Code : CC(O)(C)C#CC1=CC(Br)=CN=C1N
MDL No. :MFCD19689609
InChI Key :ZJDLSBLSLLRJJW-UHFFFAOYSA-N
Pubchem ID :58129303

Safety of [ 1262985-25-0 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H302-H315-H319
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330

Application In Synthesis of [ 1262985-25-0 ]

* 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 [ 1262985-25-0 ]

[ 1262985-25-0 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 1262985-25-0 ]
  • [ 1210838-82-6 ]
YieldReaction ConditionsOperation in experiment
With lithium hydroxide; In 1-methyl-pyrrolidin-2-one; water; at 60 - 75℃; under 37.5038 - 75.0075 Torr; Example 7; a) Preparation of 5-bromo-7-azaindole (3 or Ia) from isolated 2-amino-5-bromo-3-iodopyridine; A suspension of 2-amino-5-bromo-3-iodopyridine (5.0 g, 16.7 mmol), bis-(triphenylphosphine)-palladium(II)-dichloride (43 mg, 0.061 mmol), copper(I)iodide (29.4 mg, 0.15 mmol) and triethylamine (2.21 g, 21.8 mmol) in dichloromethane (20 mL) was treated at 23 to 30 C. within 1 to 2 hours with a solution of 1,1-dimethyl-2-propyn-1-ol (1.85 g, 21.7 mmol) in dichloromethane (10 mL) and the resulting mixture was stirred at 25 C. for 4 hours. The mixture was diluted with dichloromethane (10 mL) and washed with water (2×25 mL). The organic phase was then treated with 1 M HCl (40 mL). The layers were separated and the organic layer was extracted with 1 M HCl (15 mL). The combined product containing aqueous layers were washed with dichloromethane (2×8 mL). The pH of the aqueous layer was adjusted to pH 7-9 by the drop wise addition of sodium hydroxide solution (28% in water). The resulting suspension was stirred at 20 C. over night and the crystals were then filtered off and washed with water (2×5 mL). The wet crystals were dissolved in N-methylpyrrolidone (50 mL) and treated within 2 hours at 60 C. and 50-100 mbar with an aqueous solution of lithium hydroxide (2.4 M, 32 mL). The resulting mixture was heated to 75 C. and stirred at this temperature and under reduced pressure (50-100 mbar) for 15-20 hours. Toluene (20 mL) and water (20 mL) were then added and the layers were separated. The aqueous layer was extracted with toluene (3×25 mL). The combined organic layers were washed with water (3×10 mL) and then concentrated to dryness. The residue was dissolved in N-methylpyrrolidone (50 mL) and treated at 60 C. with potassium tert.-butylate (3.52 g, 30.7 mmol). After stirring for 3 hours at 60 C., the mixture was cooled to ambient temperature and diluted with toluene (40 mL) and water (40 mL). The aqueous layer was separated and back extracted with toluene (3×50 mL). The combined toluene layers were washed with water (3×10 mL) and then concentrated to dryness. The residue was dissolved in a hot mixture of toluene and n-heptane (20 mL). The clear solution was cooled to -5 C. within 4 to 6 hours whereupon crystals precipitated. The suspension was stirred at -5 C. for 2-4 hours. The crystals were filtered off, washed with heptane and dried at 45 C./<30 mbars over night to afford 5-bromo-7-azaindole (2.05 g, 62% yield) as slightly yellow crystals with a purity of 99.6% (HPLC, area %).
 

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