2-Bromo-4-chloro-6-nitrobenzenamine

A mixture of 4-chloro-2-nitrobenzenamine (5.1 g, 30 mmol) and N-bromosuccinimide (6.2 g, 36 mmol) in acetonitrile (50 mL) was heated at reflux for overnight. To 4-chloro-2-nitroaniline (10 g, 57.9 mmol) in acetic acid (50 mL) was cooled to°C with an ice bath. Bromine (3.28 mL, 63.7 mmol) was added dropwise and the mixture was stirred at room temperature for 1 hr, and then poured into ice water. The precipitated solid was filtered and was washed with water several times. The filter cake was re-dissolved in EtOAc, dried over sodium sulfate, filtered and concentrated in vacuogive the title compound as a yellow solid (14.66g, 100percent). ‘H NMR (400MHz, DMSO-d6) 8.08 (d, J=2.4 Hz, 1H), 8.02 (d, J=2.6 Hz, 1H), 7.27 (br s, 2H); LC-MS:method H, RT = 1.15 mm, MS (ESI) m/z: 250.9 and 252.9 (M+H)tA solution of 4-chloro-2-nitroaniline (10 g, 57, 9 mmol) in acetic acid (50 mL) was cooled to 0 °C with a ice bath. Bromine (3.28 mL, 63.7 mmol) was added dropwise, and the mixture was stirred at room temperature for 1 hr, and then poured into ice water. The precipitated solid was filtered and was washed with water several times. The filter cake was re-dissolved in EtOAc, dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound as a yellow solid (14.66g, 100percent). 1H NMR (400MHz, DMSO-d6) δ 8, 08 (d, .J = 2, 4 Hz, 1H), 8.02 (d, J = 2.6 Hz, 1H), 7.27 (br s, 2H); LC-MS: method H, RT = 1.15 min, MS (ESI) m/z: 250.9 and 252.9 (M+H)+.A solution of 4-chloro-2-nitroaniline (10 g, 57.9 mmol) in acetic acid (50 mL) wascooled to 0 °C with an ice bath. Bromine (3.28 mL, 63.7 mmol) was added dropwise, andthe mixture was stirred at room temperature for 1 hr, and then poured into ice water. The precipitated solid was filtered and was washed with water several times. The filter cake was re-dissolved in EtOAc, dried over sodium sulfate, filtered and concentrated in vacuogive the title compound as a yellow solid (14.66g, 100percent). ‘H NMR (400MHz, DMSO-d6) 8.08 (d, J=2.4 Hz, 1H), 8.02 (d, J=2.6 Hz, 1H), 7.27 (br s, 2H); LC-MS:method H, RT = 1.15 mm, MS (ESI) m/z: 250.9 and 252.9 (M+H)tA mixture of 4-chloro-2-nitroaniline (10 g) and N-bromosuccinimide (11.3 g) in acetonitrile (200 mL) was heated at 70° C. overnight. The mixture was concentrated under reduced pressure and then poured into water and let stirred at room temperature for one hour. The resulting solid was filtered, washed with water and dried. The resulting crude product loaded on silica gel was purified by chromatography (SiOa. A mixture of 4-chloro-2-nitroaniline (10 g) and /V-bromosuccinimide (11.3 g) in acetonitrile (200 ml_) was heated at 70EXAMPLE 99; (4-(4-phenyl-lH-benzordlimidazol-2-yl)-l-(7H-pyrrolor2, 3-dlpyrimidin-4-yl)piperidin-4- vDmethanamine

Molecular Weight:251.46
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:249.91447
Monoisotopic Mass:249.91447
Topological Polar Surface Area:71.8
Heavy Atom Count:12
Complexity:187
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes