4-CHLORO-5-IODO-1H-PYRROLO[2,3-B]PYRIDINE

Step B: S-BuLi (59.3 mL, 71.2 mmol, 1.4M in cyclohexane) at -78°C was added to 4-chloro-l-(triisopropylsilyl)-lH-pyrrolo[2, 3-b]pyridine (10.0 g, 32.4 mmol) in THF (100 mL), and the reaction was stirred at -78°C for 30 minutes. L (20.5 g, 80.9 mmol) in THF (50 mL) was added, and the reaction was stirred at -78°C for 20 minutes. A saturated ammonium chloride solution (50 mL) and a saturated sodium sulfite solution (50 mL) were added, and the mixture was extracted with hexanes (200 mL), washed with brine and dried over sodium sulfate. After removal of the solvent, the residue was dissolved in THF (50 mL), and TBAF (32.4 mL, 32.4 mmol) was added. The reaction was stirred at room temperature for 10 minutes, and then water (20 mL) and ethyl acetate (100 mL) were added. The organic layer was separated, washed with brine, and dried over sodium sulfate. After removal of the solvent, the residue was suspended in dichloromethane (DCM; 20 mL) and stirred for 10 minutes. The solid formed was collected by filtration to give 4-chloro-5-iodo-lH-pyrrolo[2, 3-b]pyridine (6.6 g, 73percent yield) as a solid.Synthesis of 6 sec-Butyllithium solution, 1.4M in cyclohexane (15.82ml_, 22.15mmol) was added drop wise to a solution of 4-chloro-1 -triisopropylsilanyl-1 H-pyrrolo[2, 3- b]pyridine (3.91 g, 12.77mmol) in THF (50ml_) at -78°C. The reaction was stirred at -78°C for 30 minutes and then a solution of iodine (8.03g, 31.64mmol) in THF (25ml_) was added drop wise and the reaction was stirred at -78 °C for a further 45 minutes. The reaction was quenched by the addition of saturated aqueous ammonium chloride (50ml_) and the reaction allowed to attain RT. The mixture was extracted with iso-hexane (2x75ml_) and the combined extracts washed with saturated aqueous sodium sulfite (x2) and saturated aqueous sodium chloride. The solution was dried over anhydrous MgS04 and concentrated to a colourless oil. This was taken up in THF (25ml_) and tetrabutylammonium fluoride solution, 1.0M in THF (12.7ml_, 12.7mmol) was added drop wise at RT. The reaction mixture was stirred at RT for 30 minutes and then partitioned between Hsec-Butyllithium solution, 1.4M in cyclohexane (15.82 mL, 22.15 mmol) was added drop wise to a solution of 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2, 3-b]pyridine (3.91 g, 12.77 mmol) in THF (50 mL) at -78° C.

Molecular Weight:278.48
XLogP3:2.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:277.91077
Monoisotopic Mass:277.91077
Topological Polar Surface Area:28.7
Heavy Atom Count:11
Complexity:155
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes