A Novel Method for Sulfamidating 2-Phenylisoisatin by C-H Activation
A C-H, radical technology, applied in organic chemistry, drug combination, anti-infective drugs, etc., can solve the problems of low atom utilization, cumbersome reaction steps, harsh reaction conditions, etc., to achieve high atom economy and environmental friendliness, Highly reactive and well-tolerated effects
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Embodiment 1
[0029] Example 1: Synthesis of Compound 1
[0030]
[0031] (1) 2-Phenylisoisatin (22.3 mg, 0.10 mmol), p-methylbenzenesulfonyl azide (39.5 mg, 0.20 mmol), and dichloro (pentamethylcyclopentane) were sequentially added to a clean reactor. Dienyl)iridium(III) dimer (2.0 mg, 0.005 mmol), silver bistrifluoromethanesulfonimide (7.8 mg, 0.02 mmol), acetic acid (12.0 mg, 0.20 mmol), trifluoroethanol ( 1.0 ml), replaced with argon and stirred at room temperature for 5 hours.
[0032] (2) After the reaction was completed, the solvent was removed under reduced pressure, and the residue was separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate = 10 / 1, v / v) to obtain 35.7 mg of the target product, an orange solid in a yield of 91 %; 1 H NMR (400 MHz, DMSO- d 6 ) δ 9.07 (s, 1H), 7.89– 7.85 (m, 1H), 7.78 (d, J = 7.6 Hz, 1H), 7.75 – 7.70(m, 2H), 7.60 – 7.55 (m, 1H), 7.47 (dd, J = 8.4, 1.6 Hz, 1H), 7.37 (t, J =7.2 Hz, 2H), 7.31 (d, J = 8.4 H...
Embodiment 2
[0033] Example 2: Synthesis of Compound 1
[0034]
[0035](1) 2-Phenylisoisatin (22.3 mg, 0.10 mmol), p-methylbenzenesulfonyl azide (39.5 mg, 0.20 mmol), and dichloro (pentamethylcyclopentane) were sequentially added to a clean reactor. Dienyl)iridium(III) dimer (2.0 mg, 0.005 mmol), silver tetrafluoroborate (3.9 mg, 0.02 mmol), acetic acid (12.0 mg, 0.20 mmol), trifluoroethanol (1.0 ml), argon After gas exchange, the mixture was stirred at room temperature for 5 hours.
[0036] (2) After the reaction was completed, the solvent was removed under reduced pressure, and the residue was separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate = 10 / 1, v / v) to obtain 23.5 mg of the target product, an orange solid with a yield of 60 %.
Embodiment 3
[0037] Example 3: Synthesis of Compound 1
[0038]
[0039] (1) 2-Phenylisoisatin (22.3 mg, 0.10 mmol), p-methylbenzenesulfonyl azide (39.5 mg, 0.20 mmol), and dichloro (pentamethylcyclopentane) were sequentially added to a clean reactor. Dienyl)iridium(III) dimer (2.0 mg, 0.005 mmol), silver bistrifluoromethanesulfonimide (7.8 mg, 0.02 mmol), adamantanecarboxylic acid (36.1 mg, 0.20 mmol), trifluoro Ethanol (1.0 ml) was stirred at 90° C. for 5 hours after argon replacement.
[0040] (2) After the reaction was completed, the solvent was removed under reduced pressure, and the residue was separated and purified by silica gel column chromatography (petroleum ether / ethyl acetate = 10 / 1, v / v) to obtain 30.6 mg of the target product, an orange solid with a yield of 78 %.
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