Method for preparing 5-hydroxy-7-azaindole
A technology of azaindole and hydroxyl, which is applied in the field of preparation of 5-hydroxy-7-azaindole, can solve the problems of inconvenient industrial scale-up operation, easy volatilization of boron tribromide, large amount of sodium methoxide, etc. Friendly, low cost, high yield effect
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Embodiment 1
[0049] Step S1: Preparation of 5-bromo-1-(triisopropylsilyl)-pyrrolo[2,3-b]pyridine (Ⅱ / TIPS)
[0050]
[0051] At room temperature, add 400 ml of tetrahydrofuran to a 1 L three-necked flask and start stirring. Add 5-bromo-7-azaindole (30 g, 0.15 mol) and potassium tert-butoxide (25.6 g, 0.23 mol) into the reaction flask, stir to dissolve, cool down in an ice-salt bath, and wait until the internal temperature is 0°C. The dropwise addition of triisopropylchlorosilane (30.8 g, 0.16 mol) diluted with 80 ml tetrahydrofuran was started. After the addition, keep at 0-5°C for 10-20 minutes.
[0052] Control in TLC, and the reaction ends. Add 300ml of water to the reaction bottle, stir for 15 minutes and then separate the liquids, extract the aqueous phase with methyl tert-butyl ether (200ml*2), combine the organic phases, wash the organic phase once with 500ml of saturated sodium chloride aqueous solution, and separate the liquids. After drying with anhydrous sodium sulfate, con...
Embodiment 2
[0062] Step S1: Preparation of 5-bromo-1-(tert-butoxycarbonyl)-pyrrolo[2,3-b]pyridine (Ⅱ / Boc)
[0063]
[0064] At room temperature, add 500 ml of dichloromethane into a 1 L three-necked flask and start stirring. Add 5-bromo-7-azaindole (50g, 0.25mol), 4-dimethylaminopyridine DMAP (1.55g, 13mmol), triethylamine TEA (77g, 0.76mol) in reaction flask, stir to dissolve clear Afterwards, replace with nitrogen, cool down in an ice-salt bath, and start to add di-tert-butyl dicarbonate (60.93 g, 0.28 mol) dropwise when the internal temperature is 0°C. After the addition, keep the temperature at 0-5°C for 1.5 hours.
[0065] Control in TLC, and the reaction ends. Add 500ml of water to the reaction flask, stir for 15 minutes, then separate the liquids, wash the organic phase with 500 ml of water, separate the liquids, dry the organic phase over anhydrous sodium sulfate, concentrate the solvent to obtain a crude product, and obtain the compound of formula II after purification.
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Embodiment 3
[0074] Step S1: Preparation of 5-bromo-1-(triisopropylsilyl)-pyrrolo[2,3-b]pyridine (Ⅱ / TIPS)
[0075]
[0076] At room temperature, add 4 L of tetrahydrofuran to a 10 L four-neck flask and start stirring. Add 5-bromo-7-azaindole (300 g, 1.5 mol) and potassium tert-butoxide (256 g, 2.3 mol) into the reaction flask, stir to dissolve, cool down in an ice-salt bath, and wait until the internal temperature is 0°C, start Triisopropylchlorosilane (308 g, 1.6 mol) diluted with 800 ml tetrahydrofuran was added dropwise. After the addition, keep at 0-5°C for 10-20 minutes.
[0077] Control in TLC, and the reaction ends. Add 3L of water to the reaction flask, stir for 15 minutes, then separate the liquids, extract the aqueous phase with methyl tert-butyl ether (2L*2), combine the organic phases, wash the organic phase once with 5L of saturated sodium chloride aqueous solution, and separate the liquids. After drying with anhydrous sodium sulfate, concentrate the solvent to obtain an...
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