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(2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methanamine[ No CAS ]
5-iodo-N-((2-(4-methoxyphenyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)methyl)-2-nitroaniline[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50%
With potassium carbonate; In acetonitrile; for 1.0h;Reflux;
To a stirred solution of (2-(4-methoxyphenyl)-2,3 -dihydrobenzo[b] [1 ,4]dioxin-6- yl)methanamine (0.25 g, 0.92 mmol) in acetonitrile (25 mL) was added 2-fluoro-4-iodo-1- nitrobenzene (0.27 g, 1.01 mmol) and potassium carbonate (0.26 mg, 1.85 mmol). Theresulting mixture heated to reflux. After 1 h, the mixture was allowed to cool to room temperature and was filtered. The filtrate was concentrated. Chromatographic purification of the crude product (silica gel, 10% methanol in dichloromethane elute) afforded 0.24 g (50 %) of 4-iodo-N-((2-(4-methoxyphenyl)-2,3 -dihydrobenzo[b] [1,4] dioxin-6-yl)methyl)-2- nitroaniline as a yellow solid.
2-(5-iodo-2-nitrophenyl)-2H-1,2,3-triazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
28%
With potassium fluoride; In dimethyl sulfoxide; at 70℃; for 2.0h;
To a solution of compound 81-1 (450 mg, 1.69 mmol, 1.0 eq) in DMSO (5 mL) were added compound 81-la (116 mg, 1.69 mmol, 1.0 eq) and KF (98 mg, 1.7 mmol, 1.0 eq). The reaction mixture was stirred at 70 C for 2 hours. The mixture was diluted with water (30 mL) and the resultant mixture was extracted with EA (50 mL * 3). The combined organic layers were dried over Na2SC>4, filtered and concentrated to dryness under reduced pressure. The residue was purified by column chromatography over silica gel to afford the title compound 81-2 (150 mg, 28% yield). 1HNMR (400MHz, DMSO-c) delta 8.35 (s, 1H), 8.23 (s, 2H), 8.13 (d, J = 8.3 Hz, 1H), 7.86 (d, J = 8.3 Hz, 1H).
1-(5-iodo-2-nitrophenyl)-1H-1,2,3-triazole[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
37%
With potassium fluoride; In dimethyl sulfoxide; at 70℃; for 2.0h;
To a solution of compound 89-1 (450 mg, 1.69 mmol, 1.0 eq) in DMSO (5 mL) were added compound 89-la (116 mg, 1.69 mmol, 1.0 eq) and KF (98 mg, 1.7 mmol, 1.0 eq). The reaction mixture was stirred at 70 C for 2 hours. The mixture was diluted with water (30 mL) and the resultant mixture was extracted with EA (50 mL * 3). The combined organic layers were dried over Na2S04, filtered and concentrated to dryness under reduced pressure. The residue was purified by column chromatography over silica gel to afford the title compound 89-2 (200 mg, 37% yield). 1HNMR (400MHz, DMSO-c) delta 8.75 (s, 1H), 8.33 (s, 1H), 8.23 (d, J = 8.3 Hz, 1H), 8.01 (s, 1H), 7.97 (d, J= 8.3 Hz, 1H).
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