4-CHLORO-5-AZAINDOLE

Intermediate 13-Bromo-4-chloro-lH-pyrrolo[3To a solution of 4-chloro-lH-pyrrolo[3, 2-c]pyridine ([60290-21-3], 4.74 g, 31.07 mmol) in DMF (72.16 mL) at 0 C was added NaH (60% dispersion in mineral oil, (0187) 1.74 g, 43.49 mmol) and the reaction mixture was warmed to rt and stirred for 30 min. Then the reaction mixture was cooled to 0 C and 2-chloro-N, N-dimethylacetamide ([2675-89-0], 3.83 mL, 37.28 mmol) was added and the reaction mixture was warmed to rt for 2 h. NaHC03 sat. sol. was added and the organic layer was extracted with EtOAc, then washed with water and brine, then dried over MgS04 and solvent was removed. The residue was purified by flash column chromatography (Heptane/EtOAc from 80/20 to 0/100) to obtain 1-1 (6.34 g, yield 68%) as a white solid.General procedure: To a solution of 4-chloro-lH-pyrrolo[3, 2-c]pyridine ([60290-21-3], 4.74 g, 31.07 mmol) in DMF (72.16 mL) at 0 C was added NaH (60% dispersion in mineral oil, (0187) 1.74 g, 43.49 mmol) and the reaction mixture was warmed to rt and stirred for 30 min. Then the reaction mixture was cooled to 0 C and 2-chloro-N, N-dimethylacetamide ([2675-89-0], 3.83 mL, 37.28 mmol) was added and the reaction mixture was warmed to rt for 2 h. NaHC03 sat. sol. was added and the organic layer was extracted with EtOAc, then washed with water and brine, then dried over MgS04 and solvent was removed. The residue was purified by flash column chromatography (Heptane/EtOAc from 80/20 to 0/100) to obtain 1-1 (6.34 g, yield 68%) as a white solid.General procedure: Sodium hydride (0.071 g, 1.78 mmol) was added to a stirred solution of 4-bromo-lH- pyrrolo[3, 2-c]pyridine ([1000342-68-6], 350 mg, 1.776 mmol) in DMF (11 mL) over 1 min. The mixture was stirred at rt for 1 h under nitrogen. tert-Butyl bromoacetate (0.262 mL, 1.776 mmol) was added dropwise and the mixture was stirred at rt for 12 h. (0341) The mixture was diluted in water and EtOAc. The organic layer was washed with water (x2) and brine, then separated, dried (MgS04), filtered and the solvents were evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in heptane 0/100 to 30/70). The desired fractions were collected and concentrated in vacuo to yield 1-29 (415 mg, 75%) as a white solid.

4-Chloro-1H-pyrrolo[3,2-c]pyridine is an intermediate used in the synthetic preparation of potent gp120-CD4 inhibitors.

Molecular Weight:152.58
XLogP3:1.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:152.0141259
Monoisotopic Mass:152.0141259
Topological Polar Surface Area:28.7
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes