6-CHLORO-2-METHYLINDOLE

To a stirred solution of compound 5 (2.3 g, 8.12 mmol) in CH2C12 (40 mL) under inert atmosphere was added TFA (7.5 mL) at RT. The reaction mixture was stirred for 2 h. The reaction progress was monitored by TLC; after reaction completion, the reaction mixture was quenched with water (40 mL) and extracted with CH2C12 (2 x 50 mL). The combined organic extracts were washed with saturated NaHCO3 solution (40 mL), brine solution (40 mL), dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude material. The crude material was recrystallized with 5percent EtOAc/ hexanes to afford compound 6 (1 g, 77percent) as an off-white solid. 1H NMR (500 MHz, DMSO-d6): ö 11.02 (br s, 1H), 7.36 (d, J= 8.0 Hz, 1H), 7.25 (s, 1H), 6.90 (d, J= 8.5 Hz, 1H), 6.11 (s, 1H), 2.34 (s, 3H); LC-MS: 93.5percent; (M-H) Found=164; (column: X Bridge C-18, 50 x 3.0 mm, 3.5 tm); RT 3.99 mm. 5 mMNH4OAc: ACN; 0.8 mL/min).A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1, 2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C. A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1, 2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C. A solution of 1.60 g (8.81 mmol) (6-chloro-1H-indol-2-yl)-methanol in 5 ml 1, 2-dichloroethane was added to a mixture of 80.0 ml trifluoroacetic acid and 32.0 ml triethylsilane at 65° C. C. 6-Chloro-2-methyl-1H-indole.-1-[2-(tert-Butoxycarbonylamino)-4-chlorophenyl]-2-butanone (3.49 g, 0.0123 mol) was treated with 10 mL of trifluoroacetic acid as described in Example 2, Part E, and the product chromatographed on silica and eluted with a gradient solvent (toluene'5% EtOAc/toluene) to give 1.2 g (59% yield) of To a solution of To a solution of 1-(4-chloro-2-nitrophenyl)propan-2-one (10.0 g, 46.9 mmol) in EtOH/H2O (1:1, 50 ml) were added, at 0 C., glacial acetic acid (50 ml) and iron powder (12.4 g, 234.7 mmol). The reaction mixture obtained was then stirred at 100 C. for 4 h. The mixture was concentrated, and the residue was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over Na2SO4 and then concentrated. The residue was purified by column chromatography purification with a hexane/ethyl acetate gradient as eluent. MH+: 166; 1H-NMR (400 MHz, CDCl3): delta 2.42 (s, 3H), 7.00-7.02 (dd, J=1.84 & 8.36 Hz, 1H), 7.25 (s, 1H), 7.37-7.39 (d, J=8.36 Hz, 1H), 7.84 (bs, 1H).

Molecular Weight:165.62
XLogP3:3.2
Hydrogen Bond Donor Count:1
Exact Mass:165.0345270
Monoisotopic Mass:165.0345270
Topological Polar Surface Area:15.8
Heavy Atom Count:11
Complexity:149
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes