2,3,4,5-tetrahydropyrido[4,3-b]indol-1-one

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

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

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: 2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one (559 mg) was treated with sodium hydride (73% dispersion in oil; 197 mg) and was then stirred with benzyl bromide (513 mg) at room temperature for 30 min. Purification by FCC eluting with dichloromethan: ethanol (80:1) gave the title compound (347 mg), m.p. 209°-212°. Purification by FCC eluting with dichloromethan: ethanol (80:1)

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

Procedure: 2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one (559 mg) was treated with sodium hydride (73% dispersion in oil; 197 mg) and was then stirred with benzyl bromide (513 mg) at room temperature for 30 min. Purification by FCC eluting with dichloromethan: ethanol (80:1) gave the title compound (347 mg), m.p. 209°-212°. Purification by FCC eluting with dichloromethan: ethanol (80:1)

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

Procedure: 2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one (931 mg) was treated with sodium hydride (73% dispersion in oil; 328 mg) and was then stirred with 2-bromopropane (615 mg) at room temperature for 72 h. Purification by FCC eluting with System A (200:8:1) gave a foam (324 mg) which was further purified by recrystallisation from ethyl acetate: hexane (1:1) to give the title compound (249 mg), t.l.c. (System A, 100:8:1) Rf 0.58. Purification by FCC eluting with System A (200:8:1)

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

Procedure: 2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one (931 mg) was treated with sodium hydride (73% dispersion in oil; 328 mg) and was then stirred with 2-bromopropane (615 mg) at room temperature for 72 h. Purification by FCC eluting with System A (200:8:1) gave a foam (324 mg) which was further purified by recrystallisation from ethyl acetate: hexane (1:1) to give the title compound (249 mg), t.l.c. (System A, 100:8:1) Rf 0.58. Purification by FCC eluting with System A (200:8:1)

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

Procedure: 2,3,4,5-Tetrahydro-1H-pyrido[4,3-b]indol-1-one (931 mg) was treated with sodium hydride (60% dispersion in oil; 400 mg) and was then stirred with ethyl iodide (10% v/v solution in DMF; 4 ml) to give the title compound (758 mg), m.p. 203°-204.5°.

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

Procedure: a solution of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (1.12 g) in dry DMF (60 ml) was treated with sodium hydride (60% dispersion in oil; 480 mg) and the resulting mixture was stirred under nitrogen until effervescence ceased. The mixture was then cooled to 0° and benzyl (chloromethyl) ether (10% w/v solution in DMF; 0,835 ml) was added over 10 min. Stirring was continued for a further 5 min and then water (10 ml) was added. The reaction mixture was concentrated in vacuo to give an oil which was dissolved in ethyl acetate (100 ml) and washed with water (3×100 ml). The organic phase was dried and adsorbed onto FCC silica. Purification by FCC eluting with System A (150:8:1) gave the title compound 1.1 g), m.p. 133°-135°. The mixture was then cooled to 0° Stirring The reaction mixture was concentrated in vacuo to give an oil which washed with water (3×100 ml) The organic phase was dried Purification by FCC eluting with System A (150:8:1)

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

Procedure: a solution of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (1.12 g) in dry DMF (60 ml) was treated with sodium hydride (60% dispersion in oil; 480 mg) and the resulting mixture was stirred under nitrogen until effervescence ceased. The mixture was then cooled to 0° and benzyl (chloromethyl) ether (10% w/v solution in DMF; 0,835 ml) was added over 10 min. Stirring was continued for a further 5 min and then water (10 ml) was added. The reaction mixture was concentrated in vacuo to give an oil which was dissolved in ethyl acetate (100 ml) and washed with water (3×100 ml). The organic phase was dried and adsorbed onto FCC silica. Purification by FCC eluting with System A (150:8:1) gave the title compound 1.1 g), m.p. 133°-135°. The mixture was then cooled to 0° Stirring The reaction mixture was concentrated in vacuo to give an oil which washed with water (3×100 ml) The organic phase was dried Purification by FCC eluting with System A (150:8:1)

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

Procedure: Dimethylsulphate (2.28 ml) was added over 5 min to a stirred mixture of 2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indol-1-one (3 g), acetone (12 ml) and 20% w/v aqueous sodium hydroxide (9 ml) at ca. 50°. The mixture was heated at reflux for 10 min. Further sodium hydroxide (6 ml) was added and the mixture was heated at reflux for 5 min. On cooling a solid crystallised. Water (10 ml) was added and the mixture was filtered. The solid was washed with water (2×20 ml), and dried in vacuo 45° to give the title compound (3.16 g). The t.l.c. data for this material were consistent with those obtained for the product of Example 1. at ca. 50° The mixture was heated at reflux for 10 min the mixture was heated at reflux for 5 min On cooling a solid crystallised Water (10 ml) was added the mixture was filtered The solid was washed with water (2×20 ml) dried in vacuo 45°