Methanol → HCID 71574456, compound

HRID 2369339Notes

Reaction equation

HRID 2369339 reaction equation
[H-].[Na+].[CH3:3][C:4]1[N:19]2[C:7]([CH2:8][C:9]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[NH:11][C:10]=3[CH2:18]2)=[C:6]([C:20]([O:22][CH3:23])=[O:21])[C:5]=1[C:24]([O:26][CH3:27])=[O:25].I[CH3:29].CO>CN(C=O)C>[CH3:3][C:4]1[N:19]2[C:7]([CH2:8][C:9]3[C:17]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[N:11]([CH3:29])[C:10]=3[CH2:18]2)=[C:6]([C:20]([O:22][CH3:23])=[O:21])[C:5]=1[C:24]([O:26][CH3:27])=[O:25]

Participants

6

Reactant 4

HCID 887MethanolHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86690042HCID 86690042, compound

Product 1

HCID 71574456HCID 71574456, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of NaH (0.63 g, 26.5 mmol) in dry DMF (150 ml) was added portionwise dimethyl 3-methyl-6,11-dihydro-5H-indolizino[6,7-b]indole-1,2-dicarboxylate (6 g, 17.7 mmol) at 0° C. to 5° C. After being stirred for 15 min, iodomethane (2.5 g, 17.7 mmol) was added and the reaction mixture and was stirred for additional 1 h in an ice bath. After being stirred at room temperature for 9 h, methanol was added into the reaction mixture and then evaporated to dryness in vacuo. The residue was recrystallized from MeOH to give dimethyl 3,6-dimethyl-6,11-dihydro-5H-indolizino[6,7-b]indole-1,2-dicarboxylate, 5.8 g (94%); mp 240-241° C. 1H NMR (DMSO-d6) δ 2.45 (3H, s, Me), 3.73 (6H, s, COOMe and Me), 3.74 (3H, s, COOMe), 4.16 (2H, t, J=3.4 Hz, CH2), 5.27 (2H, t, J=3.4 Hz, CH2), 7.05-7.09 (1H, m, ArH), 7.17-7.21 (1H, m, ArH), 7.48 (1H, d, J=8.2 Hz, ArH), 7.53 (1H, d, J=7.8 Hz, ArH). Anal. Calcd for (C20H20N2O4): C, 68.17; H, 5.72; N, 7.95. Found: C, 67.79; H, 5.73; N, 7.84.

Workup

  1. stirringthe reaction mixture and was stirred for additional 1 h in an ice bath
  2. stirringAfter being stirred at room temperature for 9 h
  3. customevaporated to dryness in vacuo
  4. customThe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-851cd9e30f1346dfbcbc861163e436c0
Source dataset
uspto-grants-2014_04
Patent number
US08703951B2

Reaction notes

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