6-chloro-3,4-dihydro-1H-quinoxalin-2-one

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

Procedure: The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (200 mg, 0.55 mmol) (from example 1c supra), 6-Chloro-3,4-dihydro-1H-quinoxalin-2-one (100 mg, 0.55 mmol) and K2CO3 (150 mg, 1.09 mmol) in acetonitrile (3 mL) was stirred at room temperature for 2 hour. The mixture was concentrated in vacuo and purified by flash column chromatography to give 110 mg 6-Chloro-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-3,4-dihydro-1H-quinoxalin-2-one. MS: [M+H]+=472. The mixture was concentrated in vacuo purified by flash column chromatography

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

Procedure: The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (200 mg, 0.55 mmol) (from example 1c supra), 6-Chloro-3,4-dihydro-1H-quinoxalin-2-one (100 mg, 0.55 mmol) and K2CO3 (150 mg, 1.09 mmol) in acetonitrile (3 mL) was stirred at room temperature for 2 hour. The mixture was concentrated in vacuo and purified by flash column chromatography to give 110 mg 6-Chloro-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-3,4-dihydro-1H-quinoxalin-2-one. MS: [M+H]+=472. The mixture was concentrated in vacuo purified by flash column chromatography

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

Procedure: Sodium borohydride (5.10 g) is added to a mixture of 6-chloro-1,2-dihydroquinoxalin-2-one (5.60 g), and ethanol (200 ml). The resultant solution is stirred for 2.5 hr at 20°-25°. The material is partitioned between water and ethyl acetate, the phases are separated, the organic phase is dried over magnesium sulfate and concentrated under reduced pressure to give a solid which is recrystallized from ethyl acetate/hexane to give the title compound, mp 171°-174°; IR (mineral oil) 2953, 2925, 1687, 1517, 1408, 1307 and 1299 cm-1 ; NMR (CDCl3 -MeOD) 6.6-6.8 and 3.95 δ; MS (m/z) 182, 153. The material is partitioned between water and ethyl acetate the phases are separated the organic phase is dried over magnesium sulfate concentrated under reduced pressure to give a solid which is recrystallized from ethyl acetate/hexane

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

Procedure: Sodium borohydride (5.10 g) is added to a mixture of 6-chloro-1,2-dihydroquinoxalin-2-one (5.60 g), and ethanol (200 ml). The resultant solution is stirred for 2.5 hr at 20°-25°. The material is partitioned between water and ethyl acetate, the phases are separated, the organic phase is dried over magnesium sulfate and concentrated under reduced pressure to give a solid which is recrystallized from ethyl acetate/hexane to give the title compound, mp 171-174° ; IR (mineral oil) 2953, 2925, 1687, 1517, 1408, 1307 and 1299 cm-1 ; NMR (CDCl3 -MeOD) 6.6-6.8 and 3.95 δ; MS (m/z) 182, 153. The material is partitioned between water and ethyl acetate the phases are separated the organic phase is dried over magnesium sulfate concentrated under reduced pressure to give a solid which is recrystallized from ethyl acetate/hexane

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

Procedure: Sodium borohydride (5.10 g) is added to a mixture of 6-chloro-1,2-dihydroquinoxalin-2-one (5.60 g), and ethanol (200 ml). The resultant solution is stirred for 2.5 hr at 20°-25°. The material is partitioned between water and ethyl acetate, the phases are separated, the organic phase is dried over magnesium sulfate and concentrated under reduced pressure to give a solid which is recrystallized from ethyl acetate/hexane to give the title compound, mp 171°-174°; IR (mineral oil) 2953, 2925, 1687, 1517, 1408, 1307 and 1299 cm-1 ; NMR (CDCl3 -MeOD) 6.6-6.8 and 3.95 δ; MS (m/z) 182, 153. The material is partitioned between water and ethyl acetate the phases are separated the organic phase is dried over magnesium sulfate concentrated under reduced pressure to give a solid which is recrystallized from ethyl acetate/hexane

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

Procedure: The mixture of rac-3-bromo-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one (200 mg, 0.55 mmol) (from example 1c supra), 6-Chloro-3,4-dihydro-1H-quinoxalin-2-one (100 mg, 0.55 mmol) and K2CO3 (150 mg, 1.09 mmol) in acetonitrile (3 mL) was stirred at room temperature for 2 hour. The mixture was concentrated in vacuo and purified by flash column chromatography to give 110 mg 6-Chloro-4-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-3,4-dihydro-1H-quinoxalin-2-one. MS: [M+H]+=472. The mixture was concentrated in vacuo purified by flash column chromatography