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I. Preparation of Compound 613. A mixture of 3-(6-Bromo-1 H-benzoimidazol-2-yl)-2-aza-bicyclo[2.2.1]heptane-2- carboxylic acid ferf-butyl ester 618 (264 mg, 0.673 mmol), benzene-1 , 4-diboronic acid dipinocal ester (5 eq., 3.36 g, 6.95 mmol), tetrakis(triphenylphosphine)palladium (5percent, 39 mg) and 2M potassium carbonate aqueous solution (3 eq., 1.01 ml_) in 5 mL DME was heated to 90°C under Ar for 4 hours. The reaction mixture was cooled and diluted in ethyl acetate and washed with saturated sodium bicarbonate solution. The organic layer dried (MgS04), concentrated and purified by flash column chromatography (silica gel, 20 to 60percent ethyl acetate/hexane) to give 3-{6-[4-(4, 4, 5, 5-Tetramethyl-[1 , 3, 2]dioxaborolan-2-yl)-phenyl]-1 H-benzoimidazol-2-yl}-2- aza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester 613 (295 mg, yield 85percent). LCMS- ESII. 1.08 g of compound 12, [1, 1'-bis (diphenylphosphino) ferrocene] dichlorophenyl dichloromethane complex 114 mg, Fumarate borate 1.53 g, Potassium acetate 700mg, In the nitrogen under the protection of the reaction unit with a condensing device, Add 30 mL of boiled deoxygenated dioxane with stirring.Above the suspension of nitrogen protection in the 95 oil bath stir in the antiShould be 3.5 hours. Drying the reaction solution, Column chromatography (petroleum ether / ethyl acetate, 10: 1, 2: 1) gave product 13 as an off-white solid (1.16 g).(1R, 3S, 4S)-3-(6-bromo-1H-benzimidazol-2-yl)-2-azabicyclo[2.2.1]heptane-2-carboxylic acid 1, 1-dimethylethyl ester (25 g) was suspended in 1, 4 dioxane (250 ml), followed by addition of bis(pinacolate) diboron (35.5 g), dichlorobis(di-tert- butylphenylphosphine)palladium(II) catalyst (1.5 g) and potassium acetate (18 g) at room temperature and allow to raise the temperature 80-85°C for 2-3 hours till it complies the reaction. The reaction completion is confirm by TLC, the solvent (1, 4 dioxane) was distilled out under reduced pressure and the reaction mass was cooled to room temperature by adding purified water and dichloromethane, to separate the layers. The organic layer was distilled out under reduced pressure to get a residue and further it is treated with cyclohexane to get a solid. Finally, the resultant solid was filtered and dried over at 40- 50°C to obtain a titled compound (26 g).

Molecular Weight:439.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:4
Exact Mass:439.2642367
Monoisotopic Mass:439.2642367
Topological Polar Surface Area:76.7
Heavy Atom Count:32
Complexity:738
Defined Atom Stereocenter Count:3
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes