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0 °C

To a solution of 2′-formyl-biphenyl-4-carboxylic acid quinolin-7-ylamide, Example 28, (90 mg, 0.25 mmol) in MeOH (2 mL) was added sodium borohydride (20 mg, 0.51 mmol) and the mixture was stirred for 10 min at 0° C. The reaction mixture was diluted with EtOAc (50 mL) and washed with satd NH4Cl (5 mL). The EtOAc layer was separated, washed with brine, dried over MgSO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography (gradient, 40 to 90% EtOAc/hexane) to provide the title compound as a yellow amorphous solid. MS (ESI, pos. ion.) m/z: 355 (M+1).

1. washwashed with satd NH4Cl (5 mL)
2. customThe EtOAc layer was separated
3. washwashed with brine
4. dry with materialdried over MgSO4
5. filtrationfiltered
6. customThe filtrate was evaporated in vacuo
7. customthe residue was purified by silica gel column chromatography (gradient, 40 to 90% EtOAc/hexane)