7-Chloro-1,2,3,4-tetrahydroquinoline

General procedure: In a 10 mL Schlenk tube, Fe(OTf)Preparation XLIX 9-Chloro-5, 6-dihydro-4H-pyrrolo-[3, 2, 1-ij]quinoline [0348] 5-Chloro-1, 2, 3, 4-tetrahydroquinoline [0349] A mixture of 5-chloroquinoline (10.0 g) and platinum oxide (50 mg) in acetic acid was shaken under a hydrogen atmosphere at room temperature for 4 hours. The mixture was diluted with diethyl ether and filtered through Celite. The volatiles were removed under reduced pressure and the residue was partitioned between saturated aqueous sodium bicarbonate and ethyl acetate (3.x.300 mL). The organic extracts were dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified over silica gel and the fractions containing product were combined and concentrated under reduced pressure to provide 7.0 g (69percent) of the desired compound. [0350] MS (EI m/z) C9H10ClN (M+1) [0351] Ring Formation/Decarboxylation [0352] Beginning with 5-chloro-1, 2, 3, 4-tetrahydroquinoline, the title compound was prepared essentially as described in Preparation I. [0353] MS (EI m/z) C11H10ClN (M+) 192.1 [0354] Analysis for C11H10ClN: [TABLE-US-00002] Calcd: C, 68.93; H 5.25; N, 7.30; Found: C, 69.18; H, 5.25; N, 6.97.To a solution of 1 -(3-bromo- I -tetrahydropyran-4-yl-6, 7-dihydro-4H-pyrazolo [4, 3 -c]pyridin5-yl)ethanone (Intermediates I, 0.4 g, 1.2 minol) in 1, 4-dioxane (10 mL) was added 7-chloro- 1, 2, 3 , 4-tetrahydroquinoline (482 mg, 3 mmol), chloro(2-dicyc1ohexy1phosphino-2?, 6- di-i-propoxy- 1, 1 ?-biphenyl)(2-amino- 1, 1 ?-biphenyl-2-yl)palladium(1I) (95 mg, 0.12 mmol), 2-dicyclohexylphosphino-2?, 6?-di-i-propoxy- 1, 1 ?-biphenyl (67 mg, 0.12 nimol) and t-BuONa (351 rug, 3.7 mmol). The mixture was heated to 120C for 12 h under a nitrogen atmosphere. After cooling the reaction to room temperature, the mixture was filtered and concentrated invacuo. The crude residue was diluted with DCM (100 mL) and the mixture was washed with water (50 mL x 3) and brine (50 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The crude residue was purified by silica gel chromatography (DCM MeOH 50: 1) to give the title compound (320 mg, 63%) as a yellow solid. LCMS MJZ (M+H) 415.

Molecular Weight:167.63
XLogP3:2.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:167.0501770
Monoisotopic Mass:167.0501770
Topological Polar Surface Area:12
Heavy Atom Count:11
Complexity:138
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes