benzyl N-(azetidin-3-yl)carbamate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: Starting from 5-bromo-3-methoxyquinoline (WO 2007/107965) and azetidin-3-yl-carbamic acid benzyl ester (commercial) the title compound was prepared according to procedure L followed by procedure G and was isolated as a pale yellow solid (122 mg, 63% over two steps).

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

Procedure: According to procedure F and starting from trifluoromethanesulfonic acid 6-methoxy-[1,5]naphthyridin-4-yl ester (prepared according to WO 02/008224) and azetidin-3-yl-carbamic acid benzyl ester the desired intermediate was isolated after trituration with ether as a colorless solid (5.05 g, 71%).

Conditions: temp:85.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: An oven-dried vial was charged with 8-bromo-7-fluoro-2-methoxy-[1,5]naphthyridine (commercial; 2.0 g, 7.78 mmol), palladium(II) acetate (70 mg, 0.31 mmol), DPEphos (335 mg, 0.62 mmol), K3PO4 (4.13 g, 19.45 mmol) and azetidin-3-yl-carbamic acid benzyl ester (1.68 g, 8.17 mmol). The resulting mixture was purged with argon for several min. Dioxane (25 mL) was then added via syringe and the resulting suspension was purged with argon for 3 min. The mixture was then heated at 85° C. overnight. The solvent was removed in vacuo and the residue was extracted with EA/water. The org. layer was washed with brine, dried over MgSO4 and concentrated. To the resulting solid TBME and a few drops of DCM and MeOH were added and the mixture was sonicated for 5 min and filtered to afford the title intermediate as a beige solid (2.53 g, 85%). The resulting mixture was purged with argon for several min Dioxane (25 mL) was then added via syringe the resulting suspension was purged with argon for 3 min The solvent was removed in vacuo the residue was extracted with EA/water layer was washed with brine dried over MgSO4 concentrated To the resulting solid TBME and a few drops of DCM and MeOH were added the mixture was sonicated for 5 min filtered