Dimethyl acetylenedicarboxylate → dimethyl 3-(4-chlorophenyl)-6-methyl-6,11-dihydro-5H-indolizino[6,7-b]indole-1,2-dicarboxylate

HRID 2369346Notes

Reaction equation

HRID 2369346 reaction equation
[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([N:8]2[CH:20](C(O)=O)[CH2:19][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=4)[N:11]([CH3:24])[C:10]=3[CH2:9]2)=O)=[CH:4][CH:3]=1.[CH3:27][O:28][C:29]([C:31]#[C:32][C:33]([O:35][CH3:36])=[O:34])=[O:30]>>[Cl:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]2[N:8]3[C:20]([CH2:19][C:18]4[C:17]5[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=5[N:11]([CH3:24])[C:10]=4[CH2:9]3)=[C:31]([C:29]([O:28][CH3:27])=[O:30])[C:32]=2[C:33]([O:35][CH3:36])=[O:34])=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 715748272-(4-Chlorobenzoyl)-9-methyl-1,2,3,4-tetrahydro-pyrido[3,4-b]indole-3-carboxylic acid

Product 1

HCID 71574920dimethyl 3-(4-chlorophenyl)-6-methyl-6,11-dihydro-5H-indolizino[6,7-b]indole-1,2-dicarboxylate

Conditions

Temperature
80 °C

Procedure

A mixture of 2-(4-chlorobenzoyl)-9-methyl-1,2,3,4-tetra-hydropyrido[3,4-b]indole-3-carboxylic acid (4 g, 10.8 mmol), DMAD (2.3 g, 16.3 mmol) in AC20 (30 mL) was heated at 80° C. for 2 h. The reaction mixture evaporated in vacuo to dryness. The residue was recrystallized from MeOH to give dimethyl 3-(4-chlorophenyl)-6-methyl-6,11-dihydro-5H-indolizino[6,7-b]indole-1,2-dicarboxylate, 3.5 g, (72%); mp 264-265° C. 1H NMR (DMSO-d6) δ 3.60 (6H, s, 2×COOMe), 3.78 (3H, s, NMe), 4.30 (2H, s, CH2), 5.18 (2H, s, CH2), 7.06-7.10 (1H, m, ArH), 7.17-7.20 (1H, m, ArH), 7.45-7.47 (1H, m, ArH), 7.54-7.59 (5H, m, 5×ArH). Anal. Calcd for (C25H21ClN2O4): C, 66.89; H, 4.72; N, 6.24. Found: C, 66.82; H, 4.63; N, 6.24.

Workup

  1. customThe reaction mixture evaporated in vacuo to dryness
  2. customThe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-a21e1343f7934934a071e34313a85e7f
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Reaction notes

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