7-Chloro-2,3-dihydro-1H-inden-1-one

To the above crude product (Compound-II-a), dichloromethane (400 ml) was added under ice-bath bath.A solution of 11.3 g of titanium tetrachloride in 50 ml of dichloromethane was slowly added dropwise to control the internal temperature between -10 ° C and slowly warmed to room temperature and stirred. The reaction was monitored in the gas phase when the starting material was less than 3percent (about 8 hours).The reaction solution was poured into ice water (about 2 L), extracted once with dichloromethane, and the organic phases were combined.Dry over sodium sulfate, filter dry and dry to give a crude material. Spin the reaction solvent, Flash column chromatography (ethyl acetate: petroleum ether = 1:10), Obtained a pale yellow solid compound-III-a, 21.66 g, yield 65percent2-chlorobenzoic acid (100 g, 638.9 mmol) and thionyl chloride (70 mL, 958.0 mmol) in benzene were refluxed until no more gas evolution was observed. After being cooled to room temperature the mixture was concentrated under vacuum. The mixture was diluted with dichloroethane and added to a solution of AlClTo the above crude product (Compound-II-a), dichloromethane (400 ml) was added under ice-bath bath.A solution of 11.3 g of titanium tetrachloride in 50 ml of dichloromethane was slowly added dropwise to control the internal temperature between -10 C and slowly warmed to room temperature and stirred. The reaction was monitored in the gas phase when the starting material was less than 3% (about 8 hours).The reaction solution was poured into ice water (about 2 L), extracted once with dichloromethane, and the organic phases were combined.Dry over sodium sulfate, filter dry and dry to give a crude material. Spin the reaction solvent, Flash column chromatography (ethyl acetate: petroleum ether = 1:10), Obtained a pale yellow solid compound-III-a, 21.66 g, yield 65%General procedure: To a solution of 1-indanone (264 mg, 2.0 mmol) and 5-fluoropyridin-3-amine (235mg, 2.1 mmol) in 20 mL dichloroethane was added 20 g 4A molecular sieves, and the mixture was stirred at 90 C for 24 hours. The reaction was monitored by TLC. After consumption of indanone, the sieves were removes by filtration through celite, and the filtrate was evaporated to afford the imine product 4 which was used for next step without further purification.

Molecular Weight:166.60
XLogP3:2.3
Hydrogen Bond Acceptor Count:1
Exact Mass:166.0185425
Monoisotopic Mass:166.0185425
Topological Polar Surface Area:17.1
Heavy Atom Count:11
Complexity:178
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes