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

HRID 735201Notes

Reaction equation

HRID 735201 reaction equation
[NH2:1][C:2]1[C:10]2[N:9]([CH3:11])[C:8]3[CH2:12][CH2:13][N:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:15][C:7]=3[C:6]=2[CH:5]=[CH:4][CH:3]=1.B(O)(O)[C:22]1[CH:23]=[CH:24][C:25]([CH3:28])=[CH:26][CH:27]=1.C(N(CC)CC)C>C(Cl)Cl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[CH3:11][N:9]1[C:10]2[C:2]([NH:1][C:22]3[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][CH:23]=3)=[CH:3][CH:4]=[CH:5][C:6]=2[C:7]2[CH2:15][N:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:13][CH2:12][C:8]1=2

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 79799Tolylboronic acidHCID 68816953ethyl 6-amino-5-methyl-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylate

Product 1

HCID 68816344Ethyl-5-methyl-6-(4-toluidino)-1,3,4,5-tetrahydro-2H-pyrido[4,3-b]indole-2-carboxylateYield 73%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by silica gel column chromatography (20% EtOAc-Hex)

Sources & evidence

ORD record
ord-19c671a85ff049ff85911e309c1d3a66
Source dataset
uspto-grants-2009_09
Patent number
US07592454B2

Reaction notes

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