* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Reference：
[1] Journal of the Chemical Society, 1915, vol. 107, p. 940
[2] Chemische Berichte, 1899, vol. 32, p. 160
[3] Journal of the Chemical Society, 1911, vol. 99, p. 1188[4] Journal of the Chemical Society, 1911, vol. 99, p. 1374
2
[ 62-44-2 ]
[ 5211-02-9 ]
Reference：
[1] Journal of the Chemical Society, 1915, vol. 107, p. 940
[2] Journal of the Chemical Society, 1911, vol. 99, p. 1188[3] Journal of the Chemical Society, 1911, vol. 99, p. 1374
3
[ 5493-71-0 ]
[ 5211-02-9 ]
Reference：
[1] Chemische Berichte, 1899, vol. 32, p. 160
With iron; ammonium chloride; In ethanol; at 80℃; for 3.0h;
Dissolve ammonium chloride (2.7 g, 50.4 mmol) in water (10 mL), add it to a turbid solution of iron powder (942 mg, 16.8 mmol) in ethanol (30 mL), heat to 80 C and stir, add 2- (2- A solution of chloro-4-nitrophenoxy) ethyl-1-yl (1.22 g, 5.6 mmol) in ethanol (10 mL), reacted at reflux for 1 h, cooled to room temperature, filtered through celite, the filtrate was concentrated, and EA (20 mL) was added ) The residue was dissolved, washed with saturated brine (20 mL × 3), washed with water (20 mL × 2), dried over anhydrous magnesium sulfate, and column chromatography (P / E = 3: 1 1: 1) to obtain 647 mg of an off-white solid. The rate is 61.6%, melting point: 64-65 C.
7-fluoro-4-bromo-1H-indole-2-carboxylic acid ethyl ester[ No CAS ]
4-((3-chloro-4- (2-hydroxyethoxy)phenyl)amino)-7-fluoro-1H-indole-2-carboxylic acid ethyl ester[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
29.9%
With potassium phosphate; tris-(dibenzylideneacetone)dipalladium(0); DavePhos; In water; toluene; for 20.0h;Inert atmosphere; Reflux;
4-Bromo-7-fluoro-1H-indole-2-carboxylic acid ethyl ester (200 mg, 0.7 mmol) was dissolved in toluene (16 mL), and Pd2 (dba) 3 (64 mg, 0.07 mmol) and Davephos (55 mg) were sequentially added. , 0.14 mmol) and K3PO4 (446 mg, 2.1 mmol, 2.1 mL of H2O), and after stirring well, 2- (4-amino-2-chlorophenoxy) ethyl-1-yl (394 mg, 2.10 mmol) of toluene ( 4mL) solution, under the protection of argon, refluxed for 20h. Cool to room temperature, concentrate, add EA (30mL) to dissolve the residue, 5N hydrochloric acid (20mL), saturated brine (20mL × 3), extract with water (20mL × 2), dry over anhydrous magnesium sulfate, and column chromatography (P / E = 5: 1 to 3: 1) 82 mg of a yellow solid was obtained with a yield of 29.9% and melting point: 191-192 C.
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