6-Methylbenzo[b]thiophene-2-carboxylicacid

suspension of 0.745 g of palladium on 5percent wet charcoal (50percent water) in 5 ml of methanol is added in an inert atmosphere to a mixture of 1.133 g of 3-chloro-6-methyl-benzo(b)thiophene-2-carboxylic acid (18) in 17.5 ml of tetrahydrofuran, 5 ml of IN NaOH and 17.5 ml of methanol. The suspension is then maintained under stirring in a hydrogen atmosphere at ambient temperature for 18-20 hours. The mixture is rendered inert and filtered through a Celite bed, and the catalyst washed with 30 ml of methanol. The filtrate is then evaporated until dry at low pressure, and 30 ml of IN HCl and 150 ml of ethyl acetate are added to the residue. The organic phase is washed with brine (2 x) and evaporated until dry. 0.927 g of compound (1) is obtained in the form of a white solid; HPLC purity = 97percent, yield = 96.4percent.8.5 g of palladium on 5percent wet charcoal (50percent water) is added in an inert atmosphere to a mixture of 11.33 g of 3-chloro-6-methyl-benzo[b]thiophene-2-carboxylic acid (18), 135 ml of N, N-dimethylformamide, 15 ml of 3.3 M NaOH and 40 ml of methanol/water 9/1. After repeated vacuum-hydrogen cycles, the suspension is maintained under stirring in a hydrogen atmosphere at ambient temperature for 20-24 hours. The mixture is then rendered inert and filtered through a Celite bed, and the catalyst is washed with 150 ml of methanol. The filtrate is evaporated until dry; 500 ml of water and 40 ml of 1N HCl are added, and the solution is maintained under stirring for 1 hour. The suspension is filtered and the solid washed with 200 ml of water and dried. After drying, 8.71 g of compound (I) is obtained in the form of a white solid; yield=90.6percent. HPLC purity=99.3percent. MS m/z: 191 (M−H)Example 16Example 15

Molecular Weight:192.24
XLogP3:3.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:192.02450067
Monoisotopic Mass:192.02450067
Topological Polar Surface Area:65.5
Heavy Atom Count:13
Complexity:217
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes