6-CHLORO-2H-1,4-BENZOXAZIN-3(4H)-ONE

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

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

Procedure: Using 6-chloro-4H-benzo[1,4]oxazin-3-one (0.6 g, 3.3 mmol) and borane-THF (16.4 mL of a 1M solution in THF, 16.4 mmol) in THF (15 mL) to yield the title compound as a clear oil (0.16 g, 55%). δH (CDCl3) 3.35-3.47 (2H, m), 3.81 (1H, br s), 4.17-4.29 (2H, m), 6.54-6.62 (2H, m), 6.64-6.72 (1H, m).

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

Procedure: Chloroacetyl chloride (2.39 ml) in dichloromethane (25 ml) was added to a mixture of 5-chloro-2-hydroxyaniline (3.59 g), triethyl benzylammonium chloride (5.7 g) and sodium bicarbonate (8.4 g) in dichloromethane (100 ml) at 0°C. After the addition the mixture was heated to reflux for 4 hours, then cooled and concentrated. The residue was treated with water and the resultant solid washed with ether to give 6-chloro-benzo[1,4]oxazin-3-one (4.2 g, 93% yield) as a buff coloured solid; 1H NMR (270 Mz): 3.2(1H,brd), 4.42(2H,s), 6.8-7.0(3H,m) ppm. After the addition the mixture was heated to reflux for 4 hours cooled concentrated The residue was treated with water the resultant solid washed with ether

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

Procedure: Using 6-chloro-4H-benzo[1,4]oxazin-3-one (0.6 g, 3.3 mmol) and borane-THF (16.4 mL of a 1M solution in THF, 16.4 mmol) in THF (15 mL) to yield the title compound as a clear oil (0.16 g, 55%). δH (CDCl3) 3.35-3.47 (2H, m), 3.81 (1H, br s), 4.17-4.29 (2H, m), 6.54-6.62 (2H, m), 6.64-6.72 (1H, m).

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

Procedure: Using 6-chloro-4H-benzo[1,4]oxazin-3-one (0.6 g, 3.3 mmol) and borane-THF (16.4 mL of a 1M solution in THF, 16.4 mmol) in THF (15 mL) to yield the title compound as a clear oil (0.16 g, 55%). δH (CDCl3) 3.35-3.47 (2H, m), 3.81 (1H, br s), 4.17-4.29 (2H, m), 6.54-6.62 (2H, m), 6.64-6.72 (1H, m).

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

Procedure: Chloroacetyl chloride (2.39 ml) in dichloromethane (25 ml) was added to a mixture of 5-chloro-2-hydroxyaniline (3.59 g), triethyl benzylammonium chloride (5.7 g) and sodium bicarbonate (8.4 g) in dichloromethane (100 ml) at 0°C. After the addition the mixture was heated to reflux for 4 hours, then cooled and concentrated. The residue was treated with water and the resultant solid washed with ether to give 6-chloro-benzo[1,4]oxazin-3-one (4.2 g, 93% yield) as a buff coloured solid; 1H NMR (270 Mz): 3.2(1H,brd), 4.42(2H,s), 6.8-7.0(3H,m) ppm. After the addition the mixture was heated to reflux for 4 hours cooled concentrated The residue was treated with water the resultant solid washed with ether

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

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

Procedure: Potassium carbonate (0.265 g) was added to a solution of the product from step (ii) (0.44 g) and 4-fluorophenyl methyl sulfone (0.331 g) in NMP (20 ml) and the mixture heated at 120° C. for 16 h. The reaction was diluted with water and extracted with ethylacetate, the organics were dried and evaporated under reduced pressure. The residue was purified by reverse phase HPLC, yield 0.096 g. extracted with ethylacetate the organics were dried evaporated under reduced pressure The residue was purified by reverse phase HPLC, yield 0.096 g

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

Procedure: Iron powder (1.4 g) was added to a solution of the product from step (i) (1.4 g) in acetic acid (30 ml) and the mixture stirred at RT for 1 h. The mixture was filtered and the filtrate evaporated under reduced pressure. Yield 0.44 g The mixture was filtered the filtrate evaporated under reduced pressure

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

Procedure: Potassium carbonate (0.265 g) was added to a solution of the product from step (ii) (0.44 g) and 4-fluorophenyl methyl sulfone (0.331 g) in NMP (20 ml) and the mixture heated at is 120° C. for 16 h. The reaction was diluted with water and extracted with ethylacetate, the organics were dried and evaporated under reduced pressure. The residue was purified by reverse phase HPLC, yield 0.096 g. the mixture heated extracted with ethylacetate the organics were dried evaporated under reduced pressure The residue was purified by reverse phase HPLC, yield 0.096 g

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

Procedure: Iron powder (1.4 g) was added to a solution of the product from step (i) (1.4 g) in acetic acid (30 ml) and the mixture stirred at RT for 1 h. The mixture was filtered and the filtrate evaporated under reduced pressure. Yield 0.44 g The mixture was filtered the filtrate evaporated under reduced pressure

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

Procedure: Using 6-chloro-4H-benzo[1,4]oxazin-3-one (0.6 g, 3.3 mmol) and borane-THF (16.4 mL of a 1M solution in THF, 16.4 mmol) in THF (15 mL) to yield the title compound as a clear oil (0.16 g, 55%). δH (CDCl3) 3.35-3.47 (2H, m), 3.81 (1H, br s), 4.17-4.29 (2H, m), 6.54-6.62 (2H, m), 6.64-6.72 (1H, m).