Boron tribromide → Methyl 4-{[(4-tert-butylcyclohexyl)(5-hydroxy-1-methyl-1h-benzimidazol-2-yl)amino]methyl}benzoate

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Reaction Steps

To a stirring solution of the title compound of Example 14 Step C (1 mmol, 464 mg) in 5 mL of DCM at −78° C. under N2 was added dropwise BBr3 (5 mmol, 5 mL of a 1M solution in DCM). The reaction was allowed to warm to ambient temperature. After 15 min the reaction was poured into stirring NaHCO3 (gas evolution), and the product was extracted with DCM. The organic layer was dried with Na2SO4 and concentrated under reduced pressure, affording the product as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.90 (d, 2H), 7.44 (d, 2H), 7.28 (unres. m, 1H), 7.01 (d, 1H), 6.83 (dd, 1H), 4.64 (s, 2H), 3.89 (s, 3H), 3.58 (s, 3H), 3.20 (m, 1H), 2.10 (m, 2H), 1.89 (m, 2H), 1.59 (m, 2H), 0.98-1.14 (overlapping m, 3H), 0.86 (s, 9H). MS (ESI): m/z 450 (M+H). HPLC A: 2.30 min.

Provenance & Evidence