Trifluoroacetic acid → HCID 68462228, compound

Participants

Reaction Steps

Methyl 2-(8-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate was obtained from Example 7 and 8-methyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole using the method described in Example 12. To a stirred solution of methyl 2-(8-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate (0.250 g, 0.776 mmol) in dry DCM, TFA (2.5 ml, 129.81 mmol) was added and stirred for 30 min. Then triethylsilane (2.5 ml, 62.6 mmol) was added at room temperature and stirred for 2 h. The progress of the reaction was monitored by TLC and after completion, the reaction mixture was diluted with DCM and washed with saturated solution of sodium bicarbonate and the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to furnish methyl 2-(8-methyl-1,3,4,4a,5,9b-hexahydro-2H-pyrido[4,3-b]indol-2-yl)pyrimidine-5-carboxylate (69 mg, 27.5%). 1H NMR (200 MHz, CDCl3): δ 1.69 (m, 2H), 2.35 (s, 3H), 2.7 (m; 2H), 3.01 (m, 4H), 3.90 (s, 3H), 6.23 (m, 1H), 6.80 (2H, m), 8.91 (s, 2H); m/e=325 (M+1).

Provenance & Evidence