5-Fluoro-1,3-dihydro-2H-benzimidazole-2-thione

(52a) 4-fluoro-2-nitroaniline (8.00 g, 51.22 mmol) was dissolved in methanol (100 mL), and 10percent palladium-carbon powder (0.80 g) was added thereto, followed by stirring for four hours at room temperature under hydrogen atmosphere. Step 2) Synthesis of 2-chloro-5-fluoro-1H-benzo [d] imidazole To a 50 mL of reaction flask were added 5-fluoro-1H-benzo [d] imidazole-2-thiol (1.00 g, 6.57 mmol) and phosphorus oxychloride (25 mL) . The mixture was refluxed for 13 h. After the reaction is complete, the mixture was concentrated to remove excess phosphorus oxychloride. The resulting mixture was quenched with saturated sodium bicarbonate solution (15 mL) , and extracted with ethyl acetate (10 mL ' 3) . The combined organic layers were dried over anhydrous sodium sulfate and concentrated in vacuo to give the title compound as a pale yellow solid (1.03 g, 92.0%) .MS (ESI, pos. ion) m/z: 171.05 [M+H] +.(52a) EXAMPLE I 9 Preparation of 5-fluoro-2-[[(4-cyclopropylmethoxy-2-pyridinyl)methyl)thio]-1H-benzimidazole To A suspension of 5-fluoro-lJ./-benzoimidazole-2-thiol (168 mg, 1 mmol), 5-bromo-pentanoic acid ethyl ester (188 mg, 0.9 mmol, 145 ILL.) and K2CO3 (276 mg, 2 mmol) inacetone (2 ml) is refluxed for 3 h. It is cooled down and filtered over a short plug ofsilica gel and rinsed with AcOEt. The solvent is removed in vacua. The crude ispurified by flash chromatography on silica-gel (AcOEt / heptane, 1 :2), yielding the titlecompound (190 mg) in 64% as a brown oil: fo = 1.87 min (LC-2), ESI-MS (pos.): m/z297.28 [M+H]+, ESI-MS (neg.): m/z 295.30 [M-H]+; .H-NMR (CDC13): 5 (ppm) 1.25(t, 3H, CH3), 1.79 (br. t, 4H), 2.36 (br. t, 2H, CH2CO), 3.28 (br. t, 2H, SCH2), 4.14 (q, 2H, CHaO), 6.93 (dt, lHarom), 7.20 (dd, lHarom), 7.41 (dd, lHarom).

Molecular Weight:168.19
XLogP3:1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:168.01574750
Monoisotopic Mass:168.01574750
Topological Polar Surface Area:56.2
Heavy Atom Count:11
Complexity:185
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes