A kind of cobalt catalyzed formylation reaction synthetic method for formamide derivative
A cobalt-catalyzed formyl and formamide technology is applied in the preparation of organic compounds, chemical instruments and methods, and the formation/introduction of amide groups. Low, high yield, simple operation effect
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Embodiment 1
[0036] Put tetrahydroisoquinoline (26.4mg, 0.2mmol), cobalt acetate tetrahydrate (7.5mg, 0.03mmol), and a stirring bar into the reaction tube, replace the inert gas, add 1 ml of DMF, and seal the reaction tube . Place the reaction tube in an oil bath reaction pot at 150°C, stir and react for 3 hours; after cooling to room temperature, dilute with 15 mL of water, and extract 3 times with ethyl acetate, 15 mL each time; combine the extracts and dry with anhydrous sodium sulfate , filtered, and the filtrate was concentrated under reduced pressure, and the crude product was subjected to column chromatography with ethyl acetate:petroleum ether=1:3 (containing 1% triethylamine) as the eluent to obtain a pure product. Yellow oil, yield 99%. 1 H NMR (400MHz, CDCl 3 )δ8.23 (minor isomer, s, 0.36H), 8.17 (major isomer, s, 0.62H), 7.21–7.08 (m, 4H), 4.67 (major isomer, 1.29H), 4.52 (minor isomer, 0.76H), 3.76 (minor isomer, t, J=6.2Hz, 0.76H), 3.63 (major isomer, t, J=5.8Hz, 1.29H), 2...
Embodiment 2
[0038] Put 6-methoxytetrahydroisoquinoline hydrochloride (39.9mg, 0.2mmol), cobalt acetate tetrahydrate (7.5mg, 0.03mmol), and a stirring bar into the reaction tube, replace the inert gas, Add 1 mL of DMF and seal the reaction tube. Place the reaction tube in an oil bath reaction pot at 150°C, stir and react for 3 hours; after cooling to room temperature, dilute with 15 mL of water, and extract 3 times with ethyl acetate, 15 mL each time; combine the extracts and dry with anhydrous sodium sulfate , filtered, and the filtrate was concentrated under reduced pressure, and the crude product was subjected to column chromatography with ethyl acetate:petroleum ether=1:3 (containing 1% triethylamine) as the eluent to obtain a pure product. Yellow solid, melting point 63–64°C, yield 99%. 1 H NMR (400MHz, CDCl 3 )δ8.24 (minor isomer, s, 0.38H), 8.19 (major isomer, s, 0.60H), 7.06–7.01 (m, 1H), 6.80–6.76 (m, 1H), 6.67 ( d, J=10.0Hz, 1H), 4.63 (major isomer, s, 1.29H), 4.49 (minor isom...
Embodiment 3
[0040] Put 7-bromotetrahydroisoquinoline hydrochloride (49.7mg, 0.2mmol), cobalt acetate tetrahydrate (7.5mg, 0.03mmol), and a stirring bar into the reaction tube, after replacing the inert gas, add 1 mL of DMF, and seal the reaction tube. Place the reaction tube in an oil bath reaction pot at 150°C, stir and react for 3 hours; after cooling to room temperature, dilute with 15 mL of water, and extract 3 times with ethyl acetate, 15 mL each time; combine the extracts and dry with anhydrous sodium sulfate , filtered, and the filtrate was concentrated under reduced pressure, and the crude product was subjected to column chromatography with ethyl acetate:petroleum ether=1:3 (containing 1% triethylamine) as the eluent to obtain a pure product. Yellow solid, melting point 58–60°C, yield 99%. 1 H NMR (400MHz, CDCl 3 )δ8.24 (minor isomer, s, 0.36H), 8.19 (major isomer, s, 0.63H), 7.30 (dd, J=21.4, 8.8Hz, 2H), 7.02 (t, J= 8.8Hz, 1H), 4.65 (major isomer, s, 1.32H), 4.52 (minor isomer...
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