4-BROMO-7-METHYL-1H-INDOLE

A solution of 4-bromo-1 -methyl-2-nitrobenzene (1 1 .57 mmol, 2.5 g) in THF (1 16 mL) under nitrogen atmosphere was cooled to -40 A solution of 4-bromo-1-methyl-2-nitrobenzene (11.57 mmol, 2.5 g) in THF (116 mL) under nitrogen atmosphere was cooled to −40 °C and vinyl magnesium bromide (46.28 mmol, 46 mL) was added. The reaction mixture was stirred for 40 min and quenched with saturated aqueous NH4Cl. The aqueous layer was extracted with ethyl acetate twice and the combined organic layers were dried with Na2SO4, filtered and concentrated. The crude product thus obtained was dissolved in THF (35 mL) and cooled to 0 °C. 0.5 N HCl (4.4 mL) was added and the reaction mixture was stirred at 0 °C for 1 h, then it was quenched with NaHCO3 (44 mL). The aqueous layer was extracted with ethyl acetate twice and the combined organic extracts were dried with Na2SO4, filtered and concentrated. Purification of the crude material by flash chromatography over silica gel using an elution of 11percent ethyl acetate in hexanes afforded 1.05 g (Yield: 43percent) of the pure title compound 25. 1H NMR (400 MHz, CDCl3): δ 8.21 (1H, brs), 7.28-7.26 (1H, m), 7.21 (1H, d, J = 7.2 Hz), 6.87 (1H, d, J = 6.8 Hz), 6.63-6.61 (1H, m), 2.47 (3H, s).

Molecular Weight:210.07
XLogP3:3.1
Hydrogen Bond Donor Count:1
Exact Mass:208.98401
Monoisotopic Mass:208.98401
Topological Polar Surface Area:15.8
Heavy Atom Count:11
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes