6-Chloro-1H-indole-3-acetic acid

6-Chloro-1-methylindole-3-acetic acid (SR139) Sodium hydride (0.19g of 60% suspension in oil) was suspended in dry THF (10 ml). 6-Chloroindole-3-acetic acid (SR058) (100 mg, 0.48mmol) in THF (5 ml) was added dropwise and the mixture then stirred for 10 minutes. Iodomethane (0.34 g, 2.4 mmol) was then added, and the mixture stirred overnight. Excess sodium hydride was carefully destroyed by dropwise addition of water, and then the mixture was acidified (1M HCl) and extracted with ethyl acetate (3 x 50 ml), the organic layers dried over MgSO4, and the solvent evaporated to give a brown powder, yield 75 mg, 70%, m.p. 130-132C dec.; m/z 225, 223 (M+), 180, 178 (M+ - CO2H); deltaH/ppm 7.46-6.92 (4H, m, Ar-H), 3.77 (3H, s, N-Me), 3.70 (2H, s, ArCH2).Example 6(a) 6-Chloro-1-methylindole-3-acetic acid (SR139) Sodium hydride (0.19 g of 60% suspension in oil) was suspended in dry THF (10 ml). 6-Chloroindole-3-acetic acid (SR058)(100 mg, 0.48 mmol) in THF (5 ml) was added dropwise and the mixture then stirred for 10 minutes. Iodomethane (0.34 g, 2.4 mmol) was then added, and the mixture stirred overnight. Excess sodium hydride was carefully destroyed by dropwise addition of water, and then the mixture was acidified (1M HCl) and extracted with ethyl acetate (3*50 ml), the organic layers dried over MgSO4, and the solvent evaporated to give a brown powder, yield 75 mg, 70%, m.p. 130-132 C. dec.; m/z 225, 223 (M+), 180, 178 (M+-CO2H); deltaH/ppm 7.46-6.92 (4H, m, Ar-H), 3.77 (3H, s, N-Me), 3.70 (2H, s, ArCH2).Reference Example 93 Example 3(c) 6-Chloroindole-3-acetic acid (SR058) Pale pink plates, yield 14%, m.p. 183-185C (lit. 182-184C); m/z 209 (M+), 164 (M+ - CO2H); deltaH/ppm 7.66-7.06 (4H, m, ArH), 3.71 (2H, s, ArCH2); found C 57.38%, H 3.84%, N 6.67% (calculated C 57.30%, H 3.85%, N 6.68%).Example 3(c) 6-Chloroindole-3-acetic acid (SR058) Pale pink plates, yield 14%, m.p. 183-185 C. (lit. 182-184 C.); m/z 209 (M+), 164 (M+-CO2H); 5H/ppm 7.66-7.06 (4H, m, ArH), 3.71 (2H, s, ArCH2); found C, 57.38%, H, 3.84%, N, 6.67% (calculated C, 57.30%, H, 3.85%, N, 6.68%).Example 3(c) 6-Chloroindole-3-acetic acid (SR058) Pale pink plates, yield 14%, m.p. 183-185 C. (lit. 182-184 C.); m/z 209 (M+), 164 (M30-CO2H); deltaH/ppm 7.66-7.06 (4H, m, ArH), 3.71 (2H, s, ArCH2); found C 57.38%, H 3.84%, N 6.67% (calculated C 57.30%, H 3.85%, N 6.68%).216.7 g thereof are refluxed with 2.2 lt of 20% aqueous potassium hydroxide for 3 hours. The mixture is cooled to room temperature, filtered, the filtrate combined with 600 ml of water and acidified by the dropwise addition of 600 ml of concentrated hydrochloric acid while stirring at 20. The mixture is filtered, the residue washed with water, dissolved in 3 lt of diethyl ether, the solution washed with saturated aqueous sodium chloride, dried and evaporated, to yield 207 g of

Molecular Weight:209.63
XLogP3:2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:2
Exact Mass:209.0243562
Monoisotopic Mass:209.0243562
Topological Polar Surface Area:53.1
Heavy Atom Count:14
Complexity:234
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes