2-(2-fluoroethoxy)aniline

Conditions: temp:120.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of the product of Example 126, Step 1 (800 mg, 3.65, mmol) in deoxygenated toluene (15 mL) was added NaOtBu (498 mg, 5.2 mmol), BINAP (364 mg, 0.58 mmol) Pd2(dba)3 (217 mg, 0.24 mmol) and benzophenone imine (0.8 mL, 4.7 mmol). The reaction mixture was heated at 120° C. for 3 h. The crude mixture was then washed with DCM and the aqueous layer was made basic with sat. NaHCO3. The aqueous layer was extracted with DCM and the combined organic extracts were dried (Na2SO4), filtered and concentrated. The residue was purified by chromatography on silica gel (0-5% MeOH in DCM) to afford the title compound (566 mg, 90%). MS (ESI) mass calcd. C8H10FNO, 155.1. m/z found, 156.1 [M+H]+. The crude mixture was then washed with DCM The aqueous layer was extracted with DCM the combined organic extracts were dried (Na2SO4) filtered concentrated The residue was purified by chromatography on silica gel (0-5% MeOH in DCM)