3,5-dichloro-4-(4-fluorophenyl)benzaldehyde

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 4-(2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl)benzoate (27 mg, 0.084 mmol) (from Example 1-1, Step 2) and 2,6-dichloro-4′-fluorobiphenyl-4-carboxaldehyde (15 mg, 0.056 mmol) (from Step 3) in DCE (2 mL) and methanol (2 mL) in a 20 mL scintillation vial was added acetic acid (10 uL, 0.168 mmol) and MP-cyanoborohydride resin (56 mg, 0.140 mmol, 2.49 mmol/g). The mixture was shaken at room temperature for 18 hours and was then filtered to remove the resin. The volatiles were removed in vacuo and the residue was used directly in Step 5 was then filtered to remove the resin The volatiles were removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 4-(2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl)benzoate (27 mg, 0.084 mmol) (from Example 1-1, Step 2) and 2,6-dichloro-4′-fluorobiphenyl-4-carboxaldehyde (15 mg, 0.056 mmol) (from Step 3) in DCE (2 mL) and methanol (2 mL) in a 20 mL scintillation vial was added acetic acid (10 uL, 0.168 mmol) and MP-cyanoborohydride resin (56 mg, 0.140 mmol, 2.49 mmol/g). The mixture was shaken at room temperature for 18 hours and was then filtered to remove the resin. The volatiles were removed in vacuo and the residue was used directly in Step 5 was then filtered to remove the resin The volatiles were removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 4-(2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl)benzoate (27 mg, 0.084 mmol) (from Example 1-1, Step 2) and 2,6-dichloro-4′-fluorobiphenyl-4-carboxaldehyde (15 mg, 0.056 mmol) (from Step 3) in DCE (2 mL) and methanol (2 mL) in a 20 mL scintillation vial was added acetic acid (10 uL, 0.168 mmol) and MP-cyanoborohydride resin (56 mg, 0.140 mmol, 2.49 mmol/g). The mixture was shaken at room temperature for 18 hours and was then filtered to remove the resin. The volatiles were removed in vacuo and the residue was used directly in Step 5 was then filtered to remove the resin The volatiles were removed in vacuo

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of methyl 4-(2-oxo-1-oxa-3,8-diazaspiro[4.5]dec-3-yl)benzoate (27 mg, 0.084 mmol) (from Example 1-1, Step 2) and 2,6-dichloro-4′-fluorobiphenyl-4-carboxaldehyde (15 mg, 0.056 mmol) (from Step 3) in DCE (2 mL) and methanol (2 mL) in a 20 mL scintillation vial was added acetic acid (10 uL, 0.168 mmol) and MP-cyanoborohydride resin (56 mg, 0.140 mmol, 2.49 mmol/g). The mixture was shaken at room temperature for 18 hours and was then filtered to remove the resin. The volatiles were removed in vacuo and the residue was used directly in Step 5 was then filtered to remove the resin The volatiles were removed in vacuo