5-Bromo-4,7-diazaindole

Potassium tert-butoxide (3.70 g, 33.0 mmol) was dissolved in THF (80 mL)Under N2 protection, A solution of 5-bromo-3 - ((trimethylsilyl) ethynyl) pyrazine-2-amino (9.00 g, 33.0 mmol) in THF (84 mL) was slowly added dropwise over 30 min, After the dropwise addition, the mixture was stirred at room temperature for 30 min, Reflux reaction 1h, Cooled to room temperature, filtered, The filter cake was washed with ethyl acetate (200 mL)Washed with saturated brine (50 mL x 2), the aqueous phase was combined, And extracted with ethyl acetate (60 mL x 2). The organic phases were combined, The residue was subjected to column chromatography (eluent: PE / EtOAc (v / v) = 3/1) to give the title compound5.0 g of a yellow solid, yield: 76.0percent.Step 2 To a 250 ml flask, potassium tert-butoxide (4.2 g, 0.037 mole) was added followed by in THF (50 ml). To this, 5-bromo-3-((trimethylsilyl)ethynyl)pyrazine-2-amine (10.0 g, 0.037 mole) in THF (50 ml) was added dropwise at RT over 20 min under nitrogen atmosphere. The mixture was stirred 30 min at same temperature and 60 min at 65 °C. The reaction mixture was cooled to RT and diluted with ethyl acetate and filtered. The filtrate was collected and washed with water. The layers were separated and the aq. layer was re-extracted with ethyl acetate. The combined organic layer was dried over NaStep 3: Synthesis of 2-Bromo-5H-pyrrolo[2, 3-b]pyrazine.[0284] To a solution of ^-(S-Bromo-S-trimethylsilanylethynyl-pyrazin^-y^-acetamide(474 mg, 1.52 mmol) in THF (4 ml) was added dropwise a 1 M solution of tetra-n-butyl ammonium fluoride in THF (3.3 ml, 3.3 mmol). After stirring at reflux for 15 hours, thereaction mixture was concentrated in vacuum and water added. The aqueous layer wasextracted three times with dichloromethane and the combined extracts were directlyadsorbed on silica gel. Purification by silica gel chromatography with a gradient of ethylacetate/hexanes afforded the title compound (130mg, 43percent yield) as a yellow solid. A solution of N-(5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2- yl)acetamide [Intermediate AR] (2.6 g, 8.4 mmol) and tetrabutylammonium fluoride [1 M in TΗF] (18 mL, 18 mmol) in anhydrous TΗF (26 mL) was heated at 75°C for 20 h, after which it was partitioned between EtOAc and HPreparation of 2-bromo-5H-pyrrolo [3, 2-6 pyrazine (Intermediate AS) [0315] A solution of N-(5 -bromo-3 -((trimethylsilyl)ethynyl)pyrazin-2-yl)acetamide[Intermediate AR] (2.6 g, 8.4 mmol) and tetrabutylammonium fluoride [1 M in THF] (18 mL, 18 mmol) in anhydrous THF (26 mL) was heated at 75°C for 20 h, after which it was partitioned between EtOAc and HA solution of N-(5-bromo-3-((trimethylsilyl)ethynyl)pyrazin-2-yl)acetamide (2.6 g, 8.4 mmol) and tetrabutylammonium fluoride [1 M in THF] (18 mL, 18 mmol) in anhydrous THF (26 mL) was heated at 75°C for 20 h, after which it was partitioned between EtOAc and HTo a solution of intermediate I-84 (1.0 g, 3.2 mmol, 1.0 eq) in THF (8.5 mL) was added drop wise a solution TBAF (7.1 mL, 1.0 M in THF, 7.1 mmol, 2.2 eq) and the reaction mixture was refluxed for 15 hours. The crude reaction was concentrated by evaporation; the residue was dissolved in water and extracted with ethyl acetate. The combined organic layers were dried over anhydrous NaStep 2: 2-bromo-5H-pyrrolo[2, 3-b]pyrazine[00198] Potassium tert-butoxide (6.612 g, 58.92 mmol) was suspended/dissolved in dry N- methylpyrrolidinone (15mL) and stirred at 80 °C while a solution of 5-bromo-3-(2- triethylsilylethynyl)pyrazin-2-amine (9.1992 g, 29.46 mmol) in dry N-methylpyrrolidinone (50mL) was added slowly drop wise over 10 minutes. The dropping funnel was washed out with a further aliquot of dry N-methylpyrrolidinone (lOmL). The resultant was stirred at 80°C for 1.5 hours. Reaction mixture cooled to ambient then diluted with EtOAc and water and EtOAc layer washed with small portions of water (x6). Organic layer dried (MgS0

Molecular Weight:198.02
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:196.95886
Monoisotopic Mass:196.95886
Topological Polar Surface Area:41.6
Heavy Atom Count:10
Complexity:130
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes