Triethylamine → Ethyl-5-methyl-6-(4-toluidino)-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

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Reaction Steps

Ethyl 6-amino-5-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate (103 mg, 0.37 mmol) was combined with p-tolylboronic acid (100 mg, 0.74 mmol), triethylamine (75 mg, 0.74 mmol), and copper (II) acetate (68 mg, 0.37 mmol) in CH2Cl2 (2 mL) and allowed to stir for 36 h. The solvent was evaporated and the residue purified by silica gel column chromatography (20% EtOAc-Hex) affording ethyl 5-methyl-6-(4-toluidino)-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate as a green semi-solid (73 mg, 73%) yield. 1H NMR (CDCl3, 300 MHz) δ 7.32 (d, 1H, J=7.7 Hz), 7.03 (t, 1H, J=7.7 Hz), 6.97 (d, 2H, J=8.0 Hz), 6.92 (d, 1H, J=6.9 Hz), 6.54 (d, 2H, J=8.4 Hz), 5.37 (s, 1H), 4.70 (s, 2H), 4.21 (q, 2H, J=7.0 Hz), 3.88 (br. s, 2H), 3.71 (s, 3H), 2.76 (t, 2H, J=5.5 Hz), 2.24 (s, 3H), 1.30 (t, 3H, J=7.3 Hz) ppm.

Provenance & Evidence