5-chloro-2-(trifluoromethyl)benzaldehyde

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: Dissolve (5-chloro-2-trifluoromethylphenyl)-methanol (347 mg, 1.66 mmol) in dichloromethane (10 mL). Add pyridinium chlorochromate (717 mg, 3.32 mmol) and stir for 2 h. Dilute with diethyl ether and stir for 1 h. Filter and concentrate. Chromatograph on silica gel eluting with 10% ethyl acetate in hexane to give the title compound as a clear oil (285 mg, 82%). 1H NMR (400 MHz, MeOH-d4) 10.33 (s, 1H), 7.90 (s, 1H), 7.69 (d, 1H, J=8.4 Hz), 7.54 (d, 1H, J=8.4 Hz). Filter concentrate

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

Procedure: Dissolve (5-chloro-2-trifluoromethylphenyl)-methanol (347 mg, 1.66 mmol) in dichloromethane (10 mL). Add pyridinium chlorochromate (717 mg, 3.32 mmol) and stir for 2 h. Dilute with diethyl ether and stir for 1 h. Filter and concentrate. Chromatograph on silica gel eluting with 10% ethyl acetate in hexane to give the title compound as a clear oil (285 mg, 82%). 1H NMR (400 MHz, MeOH-d4) 10.33 (s, 1H), 7.90 (s, 1H), 7.69 (d, 1H, J=8.4 Hz), 7.54 (d, 1H, J=8.4 Hz). Filter concentrate

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

Procedure: The title compound was prepared from 3-(8-chloro-3-phenyl-cinnolin-4-yl)-phenylamine and 5-chloro-2-trifluoromethylbenzaldehyde according to the procedure of Step 5 Example 6. MS (ES) m/z 523.9.

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

Procedure: The title compound was prepared from [3-(3-benzyl-8-chlorocinnolin-4-yl)phenyl]amine and 5-chloro-2-trifluoromethylbenzaldehyde according to the procedure of Step 5 Example 6. MS (ESI) m/z 538.

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

Procedure: The title compound was prepared from [3-(3-benzyl-8-chlorocinnolin-4-yl)phenyl]amine and 5-chloro-2-trifluoromethylbenzaldehyde according to the procedure of Step 5 Example 6. MS (ESI) m/z 538.

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

Procedure: The title compound was prepared from 3-(8-chloro-3-phenyl-cinnolin-4-yl)-phenylamine and 5-chloro-2-trifluoromethylbenzaldehyde according to the procedure of Step 5 Example 6. MS (ES) m/z 525.1.

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

Procedure: Dissolve (5-chloro-2-trifluoromethylphenyl)-methanol (347 mg, 1.66 mmol) in dichloromethane (10 mL). Add pyridinium chlorochromate (717 mg, 3.32 mmol) and stir for 2 h. Dilute with diethyl ether and stir for 1 h. Filter and concentrate. Chromatograph on silica gel eluting with 10% ethyl acetate in hexane to give the title compound as a clear oil (285 mg, 82%). 1H NMR (400 MHz, MeOH-d4) 10.33 (s, 1H), 7.90 (s, 1H), 7.69 (d, 1H, J=8.4 Hz), 7.54 (d, 1H, J=8.4 Hz). Filter concentrate

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

Procedure: To a solution of 13 (100 mg, 0404 mmol) in toluene 5 mL was added 5-chloro-2-(trifluoromethyl)benzaldehyde 51 (84.4 mg, 0.404 mmol) and PTSA (153.9 mg, 0.809 mmol). The reaction was stirred at 120° C. for 6 h. The reaction mixture was diluted with ethyl acetate and washed with water (3×25 mL). The organic layer was dried over sodium sulphate and concentrated to get the crude compound 52. The crude 52 was purified through flash chromatography by using 100-200 mesh silica gel. The compound (E)-2-(5-chloro-2-(trifluoromethyl)benzylidene)-6-methoxy-5-morpholino-2,3-dihydro-1H-inden-1-one 52 was eluted at 28% ethyl acetate in hexane to afford yellow coloured solid. washed with water (3×25 mL) The organic layer was dried over sodium sulphate concentrated