(6-CHLORO-1H-INDOL-2-YL)-METHANOL

Light yellow solid

To a solution of 2.00 g (8.94 mmol) 6-chlorindole-2-carboxylic acid ethyl ester in 50 ml diethyl ether were added 0.475 g (12.5 mmol) lithium aluminum hydride at 0° C. To a solution of 2.00 g (8.94 mmol) 6-chlorindole-2-carboxylic acid ethyl ester in 50 ml diethyl ether were added 0.475 g (12.5 mmol) lithium aluminum hydride at 0° C. To a solution of 2.00 g (8.94 mmol) 6-chlorindole-2-carboxylic acid ethyl ester in 50 ml diethyl ether were added 0.475 g (12.5 mmol) lithium aluminum hydride at 0° C. General procedure: A solution of indole-2-carboxylate 11 (1 mmol) in THF (10 mL)was added dropwise to a suspension of LiAlH4 (0.8 mmol) in THF(20 mL) under cooling with ice-water. After stirring at rt for 5 h, thereaction mixture was quenched with water, and then was filtratedthrough a Celite pad. The filtrate was extracted with EtOAc. Theorganic layer was washed with brine, dried over Na2SO4, andevaporated in vacuo. The residue was purified by column chromatography using EtOAc-hexane as an eluent to give thealcohol 12.To a solution of 2.00 g (8.94 mmol) 6-chlorindole-2-carboxylic acid ethyl ester in 50 ml diethyl ether were added 0.475 g (12.5 mmol) lithium aluminum hydride at 0° C. To a solution of 2.00 g (8.94 mmol) 6-chlorindole-2-carboxylic acid ethyl ester in 50 ml diethyl ether were added 0.475 g (12.5 mmol) lithium aluminum hydride at 0° C. To a solution of 2.00 g (8.94 mmol) 6-chlorindole-2-carboxylic acid ethyl ester in 50 ml diethyl ether were added 0.475 g (12.5 mmol) lithium aluminum hydride at 0° C. General procedure: A solution of indole-2-carboxylate 11 (1 mmol) in THF (10 mL)was added dropwise to a suspension of LiAlH4 (0.8 mmol) in THF(20 mL) under cooling with ice-water. After stirring at rt for 5 h, thereaction mixture was quenched with water, and then was filtratedthrough a Celite pad. The filtrate was extracted with EtOAc. Theorganic layer was washed with brine, dried over Na2SO4, andevaporated in vacuo. The residue was purified by column chromatography using EtOAc-hexane as an eluent to give thealcohol 12.General procedure: 6-Fluoro-1-(p-toluenesulfonyl)indole-2-carboxylic acid (32.75 g, 98.25 mmol) was dissolved in tetrahydrofuran (400 mL) at 0 C. Lithium aluminum hydride (9.32 g, 245.63 mmol) was added to the mixture in batches and stirred at 25 C for 16 hours. TLC showed the reaction was complete, water (9.5 mL), 15% NaOH (9.5 mL) and water (28 mL) were added successively to the reaction mixture, and the mixture was filtered and the filtrate was concentrated to give the crude product. The product was purified by column chromatography (DCM: MeOH = 20: 1, 3: 1) to deliver the title compound (white solid, 5.11 g, yield 31.49%).

Molecular Weight:181.62
XLogP3:1.8
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:1
Rotatable Bond Count:1
Exact Mass:181.0294416
Monoisotopic Mass:181.0294416
Topological Polar Surface Area:36
Heavy Atom Count:12
Complexity:165
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes