5-Bromo-1H-benzimidazole

off-white powder

Step 87a: 73/4rt-butyl 5-bromo-lH-benzo[d]imidazole-l-carboxylate (Compound 0601-187)To a solution of 4-bromobenzene-l, 2-diamine (3 g, 16 mmol) in DMF (22 mL) were added trimethyl orthoformate (44 mL) and cone. HC1 (1.5 mL) and the mixture was stirred at room temperature for 1 h. The mixture was diluted with water (200 mL) and adjusted to pH7 with saturated aqueous NaHC0Step 87a: Tert-butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate (Compound 0601-187)[0581]To a solution of 4-bromobenzene-1, 2-diamine (3 g, 16 mmol) in DMF (22 mL) were added trimethyl orthoformate (44 mL) and conc. HCl (1.5 mL) and the mixture was stirred at room temperature for 1 h. The mixture was diluted with water (200 mL) and adjusted to pH7 with saturated aqueous NaHCO4-bromobenzene -l, 2-diamine (3 g, 16 mmol) in solution in DMF (22 mL) of trimethyl orthoformate (44 mL) and concentrated HCl (1.5 mL) was added, 1 hour and the mixture is stirred at room temperature did. The mixture was diluted with water (200 mL), adjusted to pH7 with saturated aqueous NaHCO3, issued extracted with ethyl acetate (200 mL). The organic layer was dried over Na2SO4, and concentrated to give 5-bromo -1H- benzo [d] imidazole as an off-white solid (3.25g, 100percent).General procedure: A mixture of o-phenylenediamine (1.0 mmol), triethyl orthoformate (1.2 mmol) and ZrClExample 8 (5)- N2 -(l-(lH-benzo[d]imidazol-5-yl)ethyl)- N4 -(5-cyclopropyl-lH-pyrazol-3-yl)- N2 - methylpyrimidine-2, 4-diamine (1-9) and (R)- N2 -(l-(lH-benzo[d]imidazol-5-yl)ethyl)- N4 -(5- cyclopropyl- 1 H-pyrazol-3 -yl)-N2-methylpyrimidine-2, 4-diamine (1-55) step 1 : A mixture of 4-bromobenzene-l, 2-diamine (4.0 g, 21.5 mmol) and formic acid (95 percent>, 100 mL) was stirred at 100 °C overnight. The reaction mixture was cooled to RT and concentrated in vacuo to afford a dark oil. The crude oil was partitioned between EtOAc (500 mL) and NH3/H20 (50 mL). The EtOAc layer was separated and concentrated in vacuo to afford 4.5 g (100percent) of 5-bromo-lH- benzo[d] imidazole (78) as brown solid: MS (ESI) m/z = 197.0 (M+l).[0990] A solution of XXXV-1 (10 g, 53.4 mmol) in HCOOH (50 mL) was heated at reflux for 2 hours, after cooled to rt, aq.NaOH (10percent) was added slowly until the mixture was basic.Then extracted with EtOAc (100 mLx3), the combined organic layers were washed with brine, dried over Na2SO4, and concentrated in vacuo to give XXXV-2 (9 g, 85percent yield).General procedure: TUD (20 mmol) was added in batches to a solution of substituted 2‑nitroanilines (5 mmol) and NaOH (20 mmol) in H2O (15 mL) and EtOH (5 mL) at 70 °C. The reaction mixture was stirred for a certain period of time as required to complete the reaction (monitored byTLC). After cooling, 10percent NaOH solutions were added until pH = 9–10, the precipitated solid was filtered off and washed with water to obtain crude product. The crude product was recrystallised from water to give a white solid. The physical and spectra data of the compounds 2a–h were as follows.

Molecular Weight:197.03
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:28.7
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes