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With hydrogenchloride; titanium(III) chloride; In water; at 25℃; for 16h;
The title compound from step 1 (3 g, 9.49 mmol) was treated with T1CI3 (7.32 g, 47.45 mmol) in a HCl solution (61.20 g, 167.86 mmol). The reaction mixture was stirred at 25 C for 16 hr. It was then poured over 2 N aqueous NaOH (150 mL) and extracted with EtOAc (150 mL). The organic phase was dried, filtered and concentrated under reduced pressure. The residue was purified by column chromatography (PE to PE/EA=5/1) to give the title compound (2 g, 36%) as a gray solid. H NMR (CDC13, 400 MHz) delta 8.10 (br s, 1 H ), 7.09-7.08 (m, 1 H), 7.02 (d, J = 1.4 Hz, 1 H), 6.54 (d, J = 1.4 Hz, 1 H), 6.44-6.43 (m, 1 H), 3.98 (br s, 2H).
Reference Example 59 6-bromo-4-phthalimido-1H-indole <strong>[350800-81-6]4-amino-6-bromo-1H-indole</strong> (300 mg) was dissolved in acetic acid (10.0 mL), phthalic anhydride (316 mg) was added, and the mixture was stirred at 90C for 4 hours. The reaction mixture was returned to room temperature, and then neutralized with an aqueous saturated sodium bicarbonate solution, followed by extraction with ethyl acetate. The organic layer was washed with water and an aqueous saturated sodium chloride solution, and dried with anhydrous sodium sulfate. The solvent was concentrated under reduced pressure to obtain the title compound (399 mg). 1H NMR (DMSO-d6) delta (ppm): 6.35(1H,s), 7.29(1H,d), 7.44(1H,t), 7.73(1H,s), 7.94-7.96(2H,m), 8.00-8.03(2H,m), 11.51(1H,brs).
With sodium hexamethyldisilazane; In pyridine; N,N-dimethyl-formamide;
N-(4-{6-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1-methyl-1H-indol-4-ylsulfamoyl}-phenyl)-acetamide. Substituting N-[4-(6-bromo-1-methyl-1H-indol-4-ylsulfamoyl)-phenyl]-acetamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> first with sodium hexamethyldisilazide and iodomethane in N,N-dimethylformamide, then with 4-acetylamino-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=275-276 C, (M+H)+=545.
With sodium hydroxide; sodium hexamethyldisilazane; In pyridine; N,N-dimethyl-formamide;
4-Amino-N-{6-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1-methyl-1H-indol-4-yl}-benzenesulfonamide. Substituting N-[4-(6-bromo-1-methyl-1H-indol-4-ylsulfamoyl)-phenyl]-acetamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> first with sodium hexamethyldisilazide and iodomethane in N,N-dimethylformamide, then with 4-acetylamino-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. Followed by treatment with aqueous sodium hydroxide. MP=243-245 C, (M+H)+=503.
N-(6-bromo-1H-indol-4-yl)-4-chloro-benzenesulfonamide[ No CAS ]
[ 98-60-2 ]
[ 350800-81-6 ]
[ 1185265-17-1 ]
Yield
Reaction Conditions
Operation in experiment
In pyridine;
4-Chloro-N-{6-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-4-yl}-benzenesulfonamide. Substituting N-(6-bromo-1H-indol-4-yl)-4-chloro-benzenesulfonamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> with 4-chloro-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=264-266 C, (M+H)+=508.
Pyridine-3-sulfonic acid {6-[7-(2,2-dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-4-yl}-amide. Substituting pyridine-3-sulfonic acid (6-bromo-1H-indol-4-yl)-amide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> with 3-pyridinesulfonyl chloride, HCl salt in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=305-307 C, (M+H)+=475.
N-{6-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-4-yl}-4-fluoro-benzenesulfonamide. Substituting N-(6-bromo-1H-indol-4-yl)-4-fluoro-benzenesulfonamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> with 4-fluoro-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=295-297 C, (M+H)+=492.
N-{6-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-4-yl}-4-methoxy-benzenesulfonamide. Substituting N-(6-bromo-1H-indol-4-yl)-4-methoxy-benzenesulfonamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> with 4-methoxy-benzenesulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=231-233 C, (M+H)+=504.
N-{6-[7-(2,2-Dimethyl-propionyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-1H-indol-4-yl}-benzenesulfonamide. Substituting N-(6-bromo-1H-indol-4-yl)-benzenesulfonamide (prepared by treatment of <strong>[350800-81-6]6-bromo-1H-indol-4-ylamine</strong> with benzene sulfonyl chloride in pyridine) for 6-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one. MP=275-285 C, (M+H)+=474.
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