Yield:6953-65-7 82%

Reaction Conditions:

in 5,5-dimethyl-1,3-cyclohexadiene at 150; for 4 h;

Steps:

Step 1: synthesis of (5-chloro-1H-benzo[djimidazol-2-yl)methanol (intermediate21 a)

21 a)A mixture of 4-chlorobenzene-1,2-diamine (105 g, 736 mmoles, 1 eq.) andhydroxyacetic acid (112 g, 2 eq.) in xylene (1500 mL) was stirred at 150 °C for 4 hours. The mixture was then cooled to 60 °C and treated with 3N HC1 (480 ml), then basified to pH=7-8 by the addition of aqueous ammonia. The mixture was filtered and the solid was collected, washed with H20 and tert-butyl methyl ether to give 123 g (82% yield) of (5 -chloro- 1 H-benzo [d]imidazo l-2-yl)methano 1 21 a.

References:

WO2014/60411,2014,A1 Location in patent:Page/Page column 58