6-BROMO-1H-INDAZOLE-3-CARBALDEHYDE
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6-BROMO-1H-INDAZOLE-3-CARBALDEHYDE
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CAS No:
885271-72-7
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Formula:
C8H5BrN2O
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Chemical Name:
6-BROMO-1H-INDAZOLE-3-CARBALDEHYDE
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Synonyms:
6-BROMO-1H-INDAZOLE-3-CARBALDEHYDE;6-BROMO-1H-INDAZOLE-3-CARBOXALDEHYDE;6-BROMO-INDAZOLE-3-CARBOXALDEHYDE;Bromoindazolecarboxaldehyde;1H-Indazole-3-carboxaldehyde,6-broMo-;1-(6-bromo-1H-indazol-3-yl)-N,N-dimethylmethanamine
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CAS No:
6-BROMO-1H-INDAZOLE-3-CARBALDEHYDE Use and Manufacturing
(1) to 70g is added in an aqueous solution of sodium nitrite of 20g compound 1 (6-bromo-indole) acetone: water (200 ml: 200 ml) solution; room temperature, in to the system by adding 2N HCl solution to pH to 2.5 the left and right; 20 min the rear, with a red brown gas desorbing, slabs system has; 10 min later, TLC detection material disappears, cessation of the reaction, adding to system 1.0L ethyl acetate (EA), two-phase separation, the organic phase with saturated sodium bicarbonate (500 ml * 2) washing, drying organic anhydrous magnesium sulfate, concentrated to obtain 22g compound 2, as a black solid.A solution of NaNO2 (704 g, 10.2 mol) in water (1 L) was added dropwise to a solution of 6-bromo-1H-indole (400 g, 2.0 mol) in acetone (7 L) at 10 °C. The reaction mixture was stirred at 10 °C for 30 mm, aqueous 3M HC1 (437 mL) was added slowly with vigorous stirring, keeping the internal temperature between 10 and 25 °C. Thesolution was stirred at 20 °C for 3 h, and concentrated while keeping the temperaturebelow 35 °C. The solid was collected by filtration. The filter cake was washed with 1:2petroleum ether:MTBE (800 mL). The solids were collected by filtration and dried undervacuum to afford the title intermediate (450 g) as a black brown solid. ‘H NMR (CH3OD, 400 MHz) ö (ppm) 7.77 (d, J= 8.8 Hz, 1H), 7.69 (s, 1H), 7.22 (dd, J 8.4, 2.4 Hz, 1H), 5.70 (s, 1H).6-Bromo-1H-indazole-3-carbaldehyde (3)
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6-BROMO-1H-INDAZOLE-3-CARBALDEHYDE
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